


Meringue

by SurlyCat



Category: Supernatural
Genre: Alternate Universe - College/University, Anal Fingering, Anal Sex, Blow Jobs, Confused Dean, Dirty Talk, Fluff, Frottage, Jimmy is a Little Shit, M/M, Mutual Masturbation, Naked Cuddling, PWP, Rimming, Schmoop, Threesome - M/M/M, Twincest, Voyeurism, cliche house parties
Language: English
Status: Completed
Published: 2014-05-16
Updated: 2014-05-19
Packaged: 2018-01-25 03:46:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 23,252
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1629848
Author URL: https://archiveofourown.org/users/SurlyCat/pseuds/SurlyCat
Summary: <blockquote class="userstuff">
              <p>Dean and Cas have been together for about six months, when Cas starts to get antsy about their sex life. The sex has been good and all, but what Dean doesn't know is that his shy, sweet little boyfriend has been holding back. One confusing spur of the moment date with his boyfriend's twin later, and Dean finds out that Cas may not be as innocent as he thought.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> This fic is completely the fault of a random dirty dream I had featuring these three fine men, and I couldn't resist adapting it into a fic. I've never written for this ship before, but I hope you enjoy it all the same...I certainly enjoyed the dream I had ;)

**_September, last year_ **

 

Cas…wasn't really a fan of parties. Small get-togethers with friends? Sure, sign him right up. But these raucous things full of sweaty drunks grinding on each other and loud shitty dance music, and a house that smelled like cheap beer and piss? No thank you. That said, the only reason he'd agreed to come to this thing was because Jimmy, his twin, had dragged him along, citing that Cas needed to at least attempt socializing instead of burying his nose in school work on a Friday night. He'd even agreed to wear something "normal" for once, and had donned one of Jimmy's old band t-shirts and a pair of regular jeans, as opposed to the tighter style he tended to favor, after Jimmy had wrinkled his nose at the nautical-striped shirt he'd intended on wearing.

"You're gonna stick out like a sore thumb if you go in looking all," Jimmy gestured vaguely, "hipster-y. If you want to be able to hide in the corner unnoticed like usual, you need to blend in."

Cas had frowned and argued that he shouldn't have to dress any differently than he normally would, but Jimmy was persuasive, and eventually Cas caved. Once they arrived at the party, Cas was glad he'd listened because Jimmy was right; this was definitely not Cas' normal crowd, and he would have most certainly drawn attention to himself. The people at this party were jovially raucous and a little rougher around the edges than he was used to.

Unsurprisingly, Jimmy was glad to make the rounds, charming people into sharing their personal booze stashes so he wouldn't have to drink that shit that passed as beer, and generally being likable. Cas did as he was prone and found a quieter corner to pass the time, talking with a few fellow students that had also been dragged to this thing by their friends. After a couple of hours, the noise and smell and general crowdedness seemed to ratchet up as the party really kicked into gear, and Cas was over it. He found Jimmy easily enough, pouring a round of shots in the kitchen, and pulled him by the elbow as soon as the round had been drunk.

Even inebriated, Jimmy could recognize that look on his brother's face: 'If we don't leave in the next five minutes, I'm going to start scowling at everything, including you.' He knew he'd reached his limit anyway and had gotten no less than five phone numbers that night, so yeah, it was time to go before it got rowdy enough for cops to get called. Jimmy hooked a finger in one of Cas' belt loops at the back and let his older brother- by three minutes- lead him through the crowd.

They were passing through the living room and nearly to the door, when Cas pulled up short, and Jimmy only narrowly avoided running him over.

"Cas, give a little warning next-" he began, but the words drifted away as he took in exactly what had made his brother stop in his tracks.

In nothing but a pair of red plaid boxers was the most beautiful man that either twin had ever laid eyes on, grinding and writhing in time with the music on another man's lap on the couch. He was clearly shit-faced, but it did nothing to dampen the wicked smile and mirthful glint in the man's eyes as he gave a rather impressive lap dance. As soon as the song was over, the man hopped up and strode over with his hand outstretched to a petite blonde who had been watching with her arms crossed over to her chest.

"Pay up, Harvelle. You should'a known better'n to tell me I would'na done it," he slurred loudly.

The blonde rolled her eyes, but produced a twenty, bypassing his hand to stick it in the waistband of his boxers. He gave her a saucy waggle of eyebrows, which only served to earn him another eyeroll and a playful smack to his bicep that made him chuckle. Then he was turning around and going back over to the couch to gather his clothes and laughing at the guy he'd been writhing on, who was an alarming shade of red and refusing to make eye contact.

The crowd that had been watching had already turned back to their own activities, but neither of the Novak twins seemed to be able to stop watching as the man redressed himself. Right about the time he'd gotten his pants pulled up and reached for the zipper, he looked up, and seeing that he still had an audience, smirked as he pulled the zipper up far too slowly before throwing a wink at the both of them.

"Oh shit," Cas breathed, as he made eye contact with beautiful grassy-green eyes.

"Yeah," Jimmy nodded, then hooked his arm in his brother's and led them out of the house.

The twins shared an apartment just down the block, so the walk back home didn't take but a few minutes. Once they got inside, a look passed between them and they both knew that neither of them were done thinking about what they'd just witnessed. Jimmy wasted no time kicking off his shoes and flopping down on the couch with a grunt, while Cas rounded up a glass of water for his brother.

When Cas got back to the living room, Jimmy's pants were already undone, and he had a hand inside them, palming himself with a lazy grin on his lips. Cas sat the water down on the end table next to his brother with a long-suffering sigh and seated himself on the other end of the couch.

"Don't give me that look, Cas. I'm not the only one that was half-hard all the way home, thinking about that lap dance," Jimmy said.

"No, but you're the only one impatient enough to not be able to wait five minutes," Cas grumped.

"Why should I? I'm drunk, I'm horny, and I'm at home. And besides, I can't help it if I can't stop imagining what that ass would've felt like rubbing on my dick," Jimmy said, ending with a shuddering breath.

Cas let out a slow breath and closed his eyes. "Dammit, Jimmy," he muttered, as that exact imagery popped into his head. First, of the stranger grinding on his brother, then himself. When it only served to make him harder, Cas gave up the pretense of being patient and undid his own pants, earning an approving hum from his brother.

"That's what I thought. Don't be a hypocrite, Cas. I know you're thinking about him riding your dick like he was fucking paid for it."

Cas moaned softly, and with only a glance between them, the twins stopped what they were doing to push their pants down and pull off their shirts. Cas took himself in hand and finally gave himself a good stroke.

"You think he's loud?" Cas asked.

"Maybe. But I bet he's a talker. Full of 'oh fucks' and 'harders'. I'd like to… _hnnng_ ," Jimmy broke off, already stroking his dick at a good pace. "I'd like to shut him up with my dick in his mouth though. God, could you imagine what he'd look like, being filled on both ends by us? Bet his ass would look so good, stretching around a cock. "

Both twins groaned as the imagery unfolded easily in their minds. Cas had never been comfortable doing much in the way of dirty talk, but he certainly had no problem with Jimmy running his mouth. More often than not, Jimmy didn't say anything that Cas wasn't thinking, anyway.

It was only a matter of minutes until Jimmy was too far gone to say much more, but Cas didn't care because his mind was full of enough filthy images to get him there. Jimmy wasn't quite as close as Cas, but Cas knew it was because of the alcohol and decided to help his brother out, sliding over to the other end of the couch and crawling in Jimmy's lap.

Jimmy gave him an appreciative grin and immediately reached down to gather both of their lengths in his hand.

"Already so wet, huh Cas?" he asked, spreading the pre-come down Cas' cock to ease the way, before starting a brutal pace. "Why is that? Been imagining what I'd look like with his cock down my throat? Or maybe the look on his face when he gets his ass eaten out."

Cas groaned out a ' _fuck, Jimmy'_ and both twins began pumping their hips into the perfect grip of Jimmy's fist. Cas was still closer though, so he leaned in and nibbled and sucked his way up Jimmy's neck, one hand moving to fist in his hair; he knew what to do. With a harsh tug to Jimmy's hair and a lick to the shell of his ear, Jimmy tensed, and Cas couldn't help but smirk as his twin shuddered and groaned. Two strokes later, Cas felt Jimmy's cock stiffen and pulse next to his own, and the sensation was enough that they were both coming then, seconds apart. Cas shivered as Jimmy worked them through it, their come mixing and sliding in a filthy wet sound.

Cas slumped against him, resting his temple against Jimmy's as they came down, humming softly as Jimmy's clean hand came up to rub little circles on Cas' lower back. After a few minutes, Cas noticed Jimmy's breathing had turned steady and his hand had drifted down to rest on Cas' ass. Cas sat up, completely unsurprised when he saw that Jimmy was about thirty seconds away from passing out, and tapped him repeatedly on the face in the most obnoxious way possible. Jimmy cracked open glassy eyes and glared at his brother.

"You're not passing out drunk and covered in come on the couch. Come on, let's go clean up," Cas said, sliding off Jimmy's lap.

Jimmy continued glaring, but Cas just huffed and rolled his eyes as he pulled his brother up from the couch. As soon as they were standing, Cas swiped the untouched water glass and pushed it into Jimmy's hand. Wordlessly, Jimmy started drinking it as they walked to the bathroom, leaving enough in the glass to swallow down the ibuprofen he knew distantly that he needed to take.

Once they were cleaned up, Cas made sure that Jimmy got into bed alright, teasing him about tucking him in. Which Jimmy steadfastly refused to agree was happening, even as Cas pulled the covers up over his brother and smoothed them out, before leaning down to peck him on the forehead. After making sure there was an emergency vomit receptacle near the bed and a fresh glass of water on the nightstand, Cas slipped out of Jimmy's room and went to his own.

As he lay in his own bed, sleep creeping up on him, Cas considered what they had in the kitchen that he could use to make a hangover breakfast the next morning. He really didn't mind taking care of his brother that way because he knew that next time it would be his turn to party, and Jimmy would be right there to return the favor.

 

**_Two Weeks Later_ **

The brothers didn't really talk about the sexy lap-dancing stranger again, at least not in such vulgar terms. When they saw him in passing on campus, they'd give each other knowing glances, but that was about it. One time, the man made eye contact with them in the library and looked as if he was trying to place them, but decided on a friendly grin and went back to his book, mouthing absently in a near obscene fashion around his pen as he worked.

It wasn't hard to find out that the man's name was Dean Winchester, and that the giant black beast of a car the Novaks had seen rolling around belonged to him. Apparently, the drunken strip-tease/lap dance had been a strange enough behavior for the man that it had garnered gossip around campus; according to Cas and Jimmy's friend Anna, Dean had never done anything so brazen, and generally tended to keep to himself, though he was known to be friendly.

Friday had rolled around again, and it was Anna that alerted them to another party going on that night. Cas was much more inclined to go to this one, because if Anna was going, then it would likely be more his speed, and Jimmy owed him from the last party; the man had, predictably, spent most of the next day waffling between whining about his hangover, and being generally grumpy about it all.

As they were getting ready that night, Jimmy didn't bother telling Cas to change outfits because he knew that the crowd at this party would be more varied than the last one. And besides, that bright blue cardigan made Cas' eyes pop and was especially striking, combined with the tight black corduroys and thin white v-neck he was wearing beneath the sweater; Cas looked good, and clearly felt more confident dressed like himself this time. Jimmy even adjusted his own style a bit, wearing a faded, tight reddish-pink t-shirt that clung in all the right places and a pair of light gray jeans that he knew made his ass look good. When Cas quirked a brow at the shirt, Jimmy shrugged.

"What? Takes a confident man to wear a pink shirt. Gives people all the right ideas," he smirked.

Cas nodded and grinned, conceding the point.

The party was already in full swing when they showed up, but the music was- thankfully- at a more tolerable level, and most of the noise was from people talking and laughing together. There was still crappy beer, but there was also a fridge full of better choices, and pitchers of what appeared to be sangria resting on the top shelf. There was also the distinct smell of weed hanging in the air, and Cas relaxed a bit because that meant that this would likely be a much more laid-back event. Jimmy grabbed a beer, while Cas allowed himself to indulge and happily accepted the rather strong screwdriver that was passed his way by a brunette with a wicked smirk that was apparently the drink master for the time being.

The party was pleasant enough, and though Jimmy was slightly bored, it was clear that Cas was enjoying himself, talking much more animatedly than he normally would to strangers, as the alcohol had loosened him up a bit. When Cas' second cup of the night ran dry, he excused himself to the kitchen and was surprised for a moment, when he saw the petite little blonde from the other party standing there, chatting with the brunette and Anna. When Anna saw him, a grin spread across her face that was impossible not to mirror, as she waved him over.

"Hey Cas, glad you made it," Anna said, leaning in to give him a one-armed hug and standing on tiptoe to peck his cheek. And even though he knew it was a friendly gesture, Cas still couldn't help the blush that rose up at the attention. The brunette smirked at him, and the blond looked at him with obvious curiosity. But then Anna was talking again, and all eyes were on her.

"Cas, this is my girlfriend, Jo," she said, gesturing to the blonde.

"Nice to finally meet you, Jo. I was beginning to wonder if Anna had made you up, considering all the praises she sings of you," Cas grinned. Frankly, he was already feeling a good buzz from the drinks and knew that he might have skipped ahead by a couple of thoughts when he'd spoken, but hoped that Jo knew what he meant.

And she must have, because she grinned at the way Anna blushed a little and bumped her shoulder against Anna's.

"You mean I've crossed so far into awesome territory that I can't be real? Aw babe, that's so sweet," Jo said with a shit-eating grin, winking at Anna.

Anna rolled her eyes fondly and hip-checked her girlfriend before moving on. "And this is Dorothy, our friend Charlie's girlfriend," she said, gesturing to the brunette, who was working on making Cas another drink.

Cas gave her a polite smile, but before he could say anything, Jo was asking Dorothy where Charlie was.

"She's on her way…her and Dean had some class thing, so they're riding together," Dorothy shrugged.

"Oh, Cas, you and Jimmy haven't met Dean yet, have you?" Anna asked excitedly. "I think you'd both really like him," she said, not giving him a chance to answer the first question.

"Is this the Dean that gave a lap dance a couple of weeks ago?" Cas asked as nonchalantly as he could manage. Anna and Dorothy laughed at that, and Jo rolled her eyes.

"Yeah, but it was a drunk-dare that he'd probably like to pretend never happened," Anna said with a little grin.

"Jo would too, considering she lost twenty bucks that night," Dorothy piped in, winking at Jo.

Cas grinned to himself, and took a sip of his drink, only barely managing to refrain from coughing at the much stronger drink. After a couple of minutes, he excused himself politely and once out of the kitchen, bee lined for Jimmy, who was leaned up against a wall in the living room talking to someone. Once he got closer though, Cas saw who it was immediately and felt a knot swell up in his throat. He and Jimmy had an understanding that if they were both interested in the same person, the person was fair game unless one of them outright asked the other not to pursue it. Which neither of them had.

Cas had to hand it to his brother; the man knew how to use his body language, and as it was, Jimmy's posture suggested everything casual and confident, his hips jutted forward just ever so slightly. Dean was definitely interested, mirroring Jimmy and unabashedly raking his eyes over his form and laughing at whatever Jimmy had said from far too close to be friendly. A small stab of jealousy flared in his gut and instead of leaving Jimmy to it like he normally would, Cas found himself walking up to the two men. As per usual, Jimmy knew that Cas was there before he'd even seen him, and gestured to the side where Cas was about to be, already introducing him.

"Dean, this is my brother, Cas," Jimmy said, turning his head just in time for Cas to stop next to him.

Dean looked between them with confused amusement. "He wasn't even standing there. How did you?" he didn't seem to know how to finish that statement, but was grinning all the same.

Cas and Jimmy couldn't help but look at each other and lightning fast, seemed to decide that they were in this one together and smirked at the underlying competitiveness in each other. They then turned their eyes as one on Dean and said, "Twins," in unison. The way Dean blinked at them had Jimmy snickering, and Cas smirking because Dean obviously was a little overwhelmed as he looked between them. Dean seemed to catch himself though, and held out a hand to Cas.

"Well, nice to meet you, Cas," Dean said, throwing a charming grin at Cas that made a blush rise up on his cheeks. God, Dean was even more attractive up close, and remembering the things that Jimmy had said two weeks ago, Cas felt the blush deepen until the tips of his ears were hot. It was mortifying, because he definitely saw Dean glance to the side of his head and grin, and Cas could practically feel Jimmy holding his breath next to him in an effort not to laugh. Of course the fucker knew what Cas was thinking, to make him go so red.

Dean was polite, engaging Cas in the conversation that Dean and Jimmy had been in, which would've felt patronizing, if it weren't for the fact that he genuinely seemed interested in what Cas had to say. Even if he did seem to stutter and fumble every time he made contact with those ridiculous green eyes. A few minutes later, Cas was surprised when Jimmy excused himself to the restroom; Jimmy never specified where he was going when he decided to walk away from a conversation, usually just giving a 'be right back'. The 'restroom' meant that Jimmy was forfeiting, and leaving Cas to it with Dean. Cas didn't think that Dean seemed to be favoring him over his brother, but then again, Cas could also be oblivious, so he figured that Jimmy must have seen something between Dean and Cas that Cas hadn't.

As it turned out, Jimmy had been right because after an hour of conversation, where Dean and Cas seemed to drift closer and closer every few minutes, it only seemed natural when Dean pulled Cas in by his belt loops to kiss him. It had also felt natural for Cas pull back and bat his eyelashes when their hips had began to rock together as they kissed; he was 'far too drunk to enjoy it properly', as he told Dean. Of course it was bullshit, as Cas was enjoying it very much, but he also wanted to Dean to _want_ him. So with the sweetest grin he could manage with all the very crass things going through his mind, Cas had given Dean his number and left him with one last filthy kiss that held all kinds of promises of more to come, if Dean could be patient.

Jimmy complimented Cas on his self-restraint later that night when they'd gotten home, but only seemed a little put out at not being the object of Dean's interest. After all, Jimmy had no real interest in dating anyone exclusively at the moment, and it was obvious with all the googly eyes between Dean and Cas that night that there was definitely more than just physical attraction going on there. Sure, Jimmy still thought Dean was hot as fuck, but he didn't begrudge his brother for finding a connection with someone and was genuinely happy for Cas when Dean called him up the following Sunday to set up a lunch date for the next day between classes. He was also wary for this random person that could potentially hurt his brother, but as long as Dean was good to Cas and made him happy, Jimmy was happy. And Dean seemed like a cool guy, so if they could all three get along together, then that would just be a bonus.


	2. Chapter 2

**Notes for the Chapter:**

> Just a little warning, from here on out, it's mostly from Dean's perspective. Chapter one was mostly just a peek into the twins' relationship before the real start of the story.

**_April, this year_ **

Standing in front of his closet, Dean was contemplating whether he should wear the mossy-green button up that got him a lot of compliments, or the cream Henley that always made Cas extra handsy. Grinning to himself, Dean grabbed the Henley and pulled it on. Not that he didn't expect handsiness from Cas by the end of the night anyway, but it never hurt to rile his boyfriend up that extra bit. So what if it was a little bit fun watching Cas get squirmy as their date night progressed? The waiting only made it that much more intense by the end of the night, when Cas was practically rubbing himself on Dean like a cat by the time they made it to the car.

Just as he went to grab for his jeans, Dean's phone blared with Cas' ringtone.

"Was just thinking 'bout you, baby. What's up?" Dean asked as he picked up, squashing the phone to his shoulder and pulling on his jeans.

A little frustrated groan sounded through the speaker before Cas spoke. "I'm really sorry Dean, but I forgot I had a group thing tonight for that project due on Monday."

Dean's face fell, disappointed, but he tried not to sound too put-out; he knew Cas wouldn't cancel without good reason.

"No, I understand. It's fine, Cas, we'll do something tomorrow, alright?"

"Are you sure you're not mad at me?"

"Pffft. I'm not mad, baby. You've been working on that thing for a month now, so do what you gotta do," Dean assured him.

There was a small pause before Cas spoke again, voice somewhat hesitant at first when it returned, then gaining confidence with each word.

"You know what? Why don't you take Jimmy? He's been wanting to see the movie too, and he's not doing anything either tonight. No sense having your night ruined and wasting movie tickets," Cas offered.

When Dean and Cas first started dating at the beginning of the school year, it had become clear within days that there wasn't going to _be_ a Dean n' Cas unless Dean got along with Jimmy, as well. Cas had very much wanted his twin's approval; the brothers were extremely close, and one was rarely seen without the other, on or off campus. Cas' worry had been mild though, because Dean and Jimmy seemed to get along easily, despite the fact that Jimmy was kind of a little shit and had delighted in messing with Dean by pretending to be Cas more than a few times, usually on the phone.

"Look Cas, I know you're trying to help, but I'm pretty sure Jimmy would kick your ass if he knew you were making plans for him to babysit me because you're gonna be busy. And I don't need a babysitter. You're not spares for each other, and I know that," Dean ended gently. It had been important to him from day one that Cas knew that Dean saw the twins as distinct individuals.

Cas huffed, and Dean could practically see the accompanying eyeroll through the phone.

"It's not like that; I'm just making a practical suggestion. And besides, it's not like it would be some hardship for you two to go out with the way you get along. I'm not blind, Dean, I know you've both got a little crush on each other."

Dean felt like the breath had been punched out of him at Cas' suggestion. Sure, Dean may have had some pretty raunchy fantasies about the twins before he'd met them, but come on! It's not like he ever expected to date either of them back then. They'd just been two ridiculously hot dudes trawling around campus that were curiously close, even for twins. How could he not have considered it? Now that he knew them both though, he'd been pretty good about not letting his thoughts wander that way because Cas and Jimmy were people that he cared about, and it seemed disrespectful to use them as spank bank material. Together, at least. And the occasional wet dream didn't count because he couldn't help those. But here was Cas being all nonchalant about the crush that had never quite gone away from that party, and Dean swallowed harshly as he scrambled for a diplomatic response.

"I'll take your silence to mean that you're panicking, but Dean, it really doesn't bother me, so calm down," Cas said fondly, interrupting Dean's thoughts. "Now, get down here and pick my brother up and go have some fun for me."

"O-okay. Well, tell him to be ready, because I was just about to roll out," Dean said, pushing down the unease he was feeling. "Oh, and Cas? Is he in earshot right now?"

"No, why?"

"What's the password?"

"Meringue, Dean," Cas drawled tiredly.

"Sorry," Dean said softly.

"It's fine. We'll talk more about this later, alright? I have to get going."

"Alright. Go get your nerd on," Dean said with a small grin, despite the way he was kind of freaking out a little at what his boyfriend could mean by the 'this' they were going to be talking about later.

Cas sighed dramatically at Dean's jab, but gave a warm goodbye and hung up.

Dean felt kind of bad now for doubting his boyfriend's sincerity to the point that he'd had to ask the password, but the exchange had sent up too many flags, in Dean's defense.

The password system had been initiated after a particularly embarrassing incident involving one of those times that Jimmy had decided to mess with him and had pretended to be Cas, making a late-night phone sex booty call. They'd only made it about three minutes in before Jimmy couldn't stifle a laugh anymore and wheezed as he'd tried to say 'I want you to lick my balls' in his imitation of Cas' voice. Dean had called him every name in the book when he realized what was going on and was pretty sure that he was going to die of embarrassment. Fortunately, Cas hadn’t asked for a play-by-play of the conversation; Dean didn't think his ego could handle it, after some of the things he'd said in those three minutes, being the one to do most of the talking. And so the password system was born, as a way for Dean to quickly identify whom he was talking to in times of doubt.

Dressed and mirror-checked, Dean gathered up his keys and headed out, reasoning with himself the whole five minutes' drive to the twins' apartment that this wouldn't be weird if Cas hadn't made it weird. Just two friends going to get some grub and watch a movie. Nothing strange, just Dean and Jimmy hanging out, like they'd done plenty of times before. By the time he'd pulled up in front of the apartment, Dean was actually feeling pretty confident, if not slightly annoyed at his boyfriend for bringing up Dean's little crush to begin with. He pointedly ignored the part where Cas had implied that the crush was mutual.

Jimmy came out moments after Dean pulled up, and Dean couldn't help but gape a little at the sight. A man after Dean's own heart, Jimmy could usually be found wearing an old band t-shirt and comfortable- if not worn-in- jeans, and Dean had thus far never seen him in anything else since that first night he talked to the twins. Yet here was in a tight, light blue button-up that was so light it was almost white and sleeves rolled to the elbow. Then he turned around to lock the door, and Dean noticed the jeans that were much tighter and newer than anything he'd ever seen the younger Novak wear. If Dean didn't know better, he'd swear it was Cas from the back, because that ass and those thighs were fucking identical. Shit, Jimmy had dressed for a fucking date. And oh god, he was hot.

It was already dark out, so there was no way that Jimmy had seen Dean gawking as he made his way to the car, and thank goodness for small mercies. He slid into the car with the ease of familiarity and buckled up before turning to smirk at Dean, like he just _knew_. But then again, Jimmy was nothing if not confident, so he probably _did_ know that Dean had been checking him out.

"So. What's for dinner?"

The neutral question put Dean at ease a bit, and he shifted the car into gear and pulled out.

"I'd planned on taking Cas to that frouffy pizza place he keeps going on about, but I don't care either way," Dean replied.

"Pizza's fine with me," Jimmy shrugged. "I'm just arm candy tonight," he teased.

Dean shot him a quick glare, but Jimmy just laughed. "Lighten up, Winchester, I'm just messing with you. I'll have you know that I make an excellent date. I keep up conversation and hold doors open and shit, and- and- you look very lovely tonight, Dean," he said with a fluttering of eyelashes and a sarcastic-sincere tone. "See? I'm even complimentary," he said, a shit-eating grin spreading on his face.

"You're such an assface," Dean grumbled. It was nothing new for Jimmy to rib at him like that, and Dean would probably be more concerned if Jimmy wasn't being…himself.

"I'll be sure to tell that to the man you're fucking, that shares said 'assface'," Jimmy chuckled.

Dean rolled his eyes, but didn't respond because it would only egg the other man on.

When they got to the restaurant, Dean sighed and barely refrained from pinching the bridge of his nose as he took in the decidedly more intimate setting the restaurant adopted at night, with the mood lighting and smooth jazz and the addition of proper tablecloths. They were seated in a booth, and before either man could say anything, the server had leaned over and lit the little votive candle that was resting in the middle of the table. Jesus Christ, this was the worst idea. Not that the server could've known that they weren't on a date, it wasn't his fault, so Dean suppressed the urge to immediately blow the candle out. Jimmy snorted quietly at the look on Dean's face as the server took their drink order.

Despite Jimmy's delight at Dean's discomfort- surprise, surprise- they managed to slip into normal conversation for them, discussing their school and work dramas, making fun of Cas' terrible taste in music, and generally just getting along. It had finally started to feel like a normal hangout time between them, until Lisa, Dean's lab partner, spotted them and came over to say hello.

"Hey, Dean," she said, with a friendly grin. Then she turned to Jimmy. "And you must be Cas. I'm Lisa, Dean's lab partner. I've heard a lot about you, you know," she said, throwing a knowing grin to Dean. "Nice to finally meet the other Novak; I have Russian Lit with Jimmy."

A denial was quick on Dean's lips, but Jimmy was faster and offered Lisa a sweet little grin that was so eerily Cas-like (and nothing like Jimmy's grin), that Dean couldn't help but do a double-take. Jimmy's foot was quick knock against Dean's in warning under the table, but his composure didn't falter.

"Likewise," Jimmy graveled in his Cas-voice, adding in a head tilt for good measure. "It's always a pleasure to meet someone that can keep Dean in line. And I hope my brother hasn't given you too much trouble."

_Holy shit, what was he doing? Was he seriously pretending to be Cas?_

Lisa laughed lightly and patted Dean on the shoulder, giving it a little squeeze. "I see you've been telling everyone I'm a hardass, then. And no, Jimmy's been great. He's kind of brilliant, actually. Must run in the family, because I've heard all about how gifted you are, as well."

Dean could see the way Jimmy was practically vibrating between wanting to preen under the misdirected compliment, and crack a dirty joke about the 'gifted' comment. Jimmy hid it all impressively well though, even managing to adopt that bashful look that Cas gets when someone compliments him. And was that a fucking blush? Was that little shit actually capable of willing himself to blush?

"Thank you, that's very kind of you," Jimmy said softly. "Don’t tell Jimmy that though, or he'll never shut up about it," he said with a small conspiratorial grin.

"Oh trust me, I won't. Don't get me wrong, I like him a lot, but he's kind of…cocky," Lisa admitted with an apologetic grin. "Well anyway, I'll leave you two to your date; just wanted to stop by and say hello. Have a good night, guys," she said, winking at Jimmy before walking off.

As soon as she was out of earshot and line of sight, Dean leaned across the table.

"What the hell was that?" Dean hissed, knocking Jimmy's foot under the table for good measure.

Jimmy just cocked an eyebrow at Dean and leaned back in his seat, all similarities to Cas gone except for, well, the twin thing.

"That was me helping you out. She clearly assumed we were on a date, so to correct her would've made you out to look like a player and a cheat, scrambling to hide a secret. Unless you'd _prefer_ to get the cold shoulder for the rest of the semester from the person helping you pass; Lisa's a good person and wouldn't look kindly on you for that. So you're welcome," Jimmy said.

Well damn. Jimmy had a point there, though it still made Dean uncomfortable with how easily the man had been able to mimic his brother. He wondered vaguely if Cas could do it too, but was pulled from his thoughts by Jimmy speaking again.

"Plus, I don't want to piss her off because I like her; she thinks I'm brilliant," Jimmy smirked.

"And cocky," Dean added.

Jimmy shrugged, grin still in place. "I've been called worse."

Dean rolled his eyes good-naturedly and they went back to their meal, which they were almost done with anyway. When the server brought the check, Jimmy snatched it up and pulled out his wallet before Dean could blink.

"Dude, I'd planned on splitting that," Dean grumbled.

"Like I said, I'm a good date," Jimmy winked. Dean had seen Jimmy's charm in action before, but it was even more alarmingly attractive, having it turned on himself; he'd almost forgotten what that was like. It was really no surprise that the man had both panties and boxers practically flying at him wherever he went.

And true to his word, Jimmy actually did hold the door open for Dean on the way out, guiding him with a hand to the small of Dean's back, earning an incredulous look for his effort. He didn't seem bothered by it though, and just walked to the car next to Dean, their shoulders bumping every few steps. They were unnecessarily close, but dammit if the fucking Novaks had zero sense of personal space, either one of them.

It wasn't the first time they'd stood so close, but there was definitely an underlying tension there that Dean hadn't felt since the first time he'd met the twins, at a party. The two of them had flirted a bit that night, as Dean met Jimmy first, but the moment that Dean had laid eyes on Cas wearing that blue cardigan and tight jeans, looking every inch the hipster type that Dean normally wouldn't give a second look, it had been over. Unlike Jimmy, Cas was shy, speaking with a formality and politeness that was kind of adorable. Now that Cas is comfortable with Dean, that sense of shyness is mostly a distant memory and the man becomes rather animated when he talks about the things he loves. And where Jimmy's eyes are bright and clever, Cas' seem deeper and filled with a warmth and soulfulness that Dean could nearly drown in; despite the identical blue color between them, they each wear it differently, attractive in their own ways.

The ride to the theater passed in a comfortable semi-silence between Dean and Jimmy, both men a bit distracted with their own thoughts. Jimmy took off to the restroom when they got inside, while Dean took care of getting their drinks, and a box of Starburst, more out of habit with Cas than anything. When Jimmy saw the box in Dean's hand as they met up in front of their designated theater, he smirked; they were both fully aware of Cas' weakness for the candy.

"Er, sorry, habit," Dean shrugged, a bit embarrassed as he held the box out. "S'cool if you don't want 'em."

Jimmy chuckled and took the box before opening the door yet again for Dean. "Don’t be sorry, it's adorable, and I don't blame you. Kind of hard to not think of Cas when you've spent the last hour looking at this mug," he said, gesturing to himself.

"You two don't normally really look all that much alike though. I mean you do, but you don't," Dean said, as they climbed the steps toward the top row, Jimmy a step behind him. Thankfully, the movie they were seeing had been out for a while, so there were only four other people in the room; Dean didn't like crowds. "That made more sense in my head," he said, frowning to himself.

Picking a seat just slightly off center, Dean flopped down and settled the drinks in the cup holders, one on each side of him. Jimmy hesitated for a split second, and then picked up the cup on Dean's right and pushed up the armrest so he could sit next to Dean, unobstructed. Dean gave him an odd look.

"It's claustrophobic, being all pinned in with the arm rests," Jimmy explained. "But anyway, what you said makes sense. If nothing else, Cas doesn't seem to know the first thing about using a razor properly," he grinned.

Dean grinned too, because that ever-present layer of stubble was actually one of those things he loved about Cas. Especially when he could feel it rasp against the insides of his thighs, or against his neck, and occasionally, against an asscheek. In fact, he was pretty sure that he still had a patch of scruff burn on the left cheek, from the night before.

Jimmy chuckled and leaned in then, to whisper. "Not very discreet, Dean."

"What are you talking about?" he asked defensively.

"Your face says it all; you were having some pretty dirty thoughts just then," Jimmy said, breath tickling at Dean's ear.

"Was not," Dean argued, completely aware that he was full of shit.

Jimmy tilted his head and shot him a dry look before leaning back in. "So you _weren't_ just thinking about the way my brother's face feels rubbing against your ass before he rims the hell out of you?"

Dean gasped and choked on his own spit, doubling over as he spluttered and wheezed, trying to catch his breath. Jimmy just rubbed a hand over his back to try and ease Dean's breath, until he seemed able to sit back up, sniffling and wiping his eyes.

"Jesus Christ, Jimmy!" Dean rasped, then cleared his throat a couple of times. "How did you…never mind," Dean cut himself off. He hadn't meant confirm Jimmy's allegation, and holy inappropriate conversations, Batman!

Jimmy snorted at Dean's slip-up. "You're easy to read, Dean. And you have a very distinct face you make when you're thinking about fucking," he murmured right in Dean's ear, voice pitching suggestively.

"Oh my god, stop," Dean pleaded, rubbing a hand over his heated face. Whether it was hot from the coughing spell, embarrassment, or the way he was getting inappropriately turned on, he couldn't tell at the moment.

Apparently satisfied at Dean's level of discomfiture, Jimmy chuckled and leaned back into his seat and took a sip of his drink. And of course the asshole seemed to be smiling around the straw. Cas had implied earlier that Jimmy had some less than platonic thoughts about him, but Dean hadn't expected Jimmy to just bust right out with that kind of suggestive shit. In hindsight it was a stupid assumption though, because Jimmy was nothing if not consistent, and the man had a flair for this sort of thing.

A minute later, Jimmy nudged him with his elbow, offering up a piece of candy as if nothing out of the ordinary was going on. Dean took one, happy for the distraction as they waited for the lights to go down. Dammit, why'd they have to show up ten minutes early? But then Jimmy popped a whole piece in his mouth, wrapper and all, making sure Dean saw him do it. Goddamned tease; Dean knew exactly what Jimmy was doing and rolled his eyes.

"What are you, thirteen? Everyone that's been through seventh grade knows how to do that," Dean muttered.

Jimmy raised his eyebrows, but didn't respond, mouth working around his Starburst. Less than five seconds later, he stuck his tongue out and okay, maybe Dean was a little impressed. Not only did the wrapper seem to be intact, but it was also folded up into a little square; he'd never quite seen that trick before. Pulling the little square off of his tongue, Jimmy winked and proceeded to chew up the candy that had been left in his mouth.

"Okay, no need to get smug over a junior high party trick," Dean said a bit gruffly. Traitorously, his brain had easily supplied all the ways that agile tongue could be put to use, and Dean internally cursed himself for being such a sucker for the stupid gimmick and those stupid attractive Novak faces.

"I don't see you trying to do it," Jimmy challenged.

In a moment of frustration with the whole confusing situation he was in, Dean leveled an unimpressed look at his friend and fired back, "Because I know I'm good at sucking cock. I don't have to make allusions."

Jimmy's eyebrows rose in surprise at Dean's unusual directness, but then lowered again as his eyes sparked with amusement. "I know. My brother is rather pleased with your skills, and I believe him."

"He's talked about that with you?" Dean asked, scandalized. He didn't think Cas was one to go around talking about their sex life.

"I was curious, so I asked. And he answered," Jimmy shrugged. "If it makes you feel better, he doesn't go around talking about it or anything. He and I just don't really have any secrets from each other. Kind of figured you knew that, though," he said, brows pinching at the end.

Nope. That was definitely news to Dean. He knew that the twins shared pretty much everything, but it had never occurred to him that Cas would talk about _that_ with his brother. The longer this 'date' went on, the more Dean was coming to the conclusion that his suspicions of the brothers' closeness wasn't just his imagination. And then with the easy 'go have fun with my brother' Cas had said on the phone…what was that? Was that some sort of permission? It was sure as shit seeming like it now the way things were adding up, and Dean wasn't sure what to do with the information because damned if that didn't mean that his boyfriend was a hell of a lot kinkier than he'd been letting on.

Before he could stew for too long, the lights blessedly went down, and the opening advertisements started up on the screen. When the reminder to silence their phones popped up, both men dutifully pulled theirs out. Dean was surprised to see two texts from Cas; he hadn't felt his phone vibrate.

>> Group ran shorter than exp., on my way home now. See you in a few hrs. <3       8: 56pm

>> Also, I really meant what I said earlier. Just relax and enjoy yourself, alright? I want you two to have fun.        9:00pm

Relax? Yeah, Dean was so not relaxed. He was the kind of person that has to be told things directly, and Cas' vagueness wasn't helping _at all_. It just seemed to ratchet up his confusion even more because that was definitely Cas reaffirming that he was okay with whatever attraction thing was going on with Dean and Jimmy, but Dean needed boundaries, dammit! And he wasn't going to bother pretending to himself that he wasn't interested in maybe having a go at both of the brothers, because come on…they were both hot as fuck, and between the way Jimmy had been whispering in his ear, and the subtle little implications of Cas' blessing, Dean was going to lose his mind if something didn't give.

Silencing his phone and putting it away, Dean glanced over to see Jimmy tapping out a message with his brows scrunched together. A moment later, his screen lit up with a new message, and he hummed contemplatively as he considered his reply. Of course he was texting Cas, who else would it be? A few more exchanges later, and Jimmy put his phone away, a small grin on his face now that made Dean all kinds of skeptical. A moment later, Jimmy laid his hand palm up on Dean's thigh and looked at him expectantly.

"I told him you're being all weird and tense, and he said it's probably my fault and to fix it. So I'm sorry. Now, hold my hand and calm the fuck down," Jimmy whispered.

Dean blinked at the hand. The fingers waggled in invitation. With a sigh, Dean caved and reluctantly threaded his fingers with Jimmy's, and they both shifted to sort of lean into each other more comfortably. It was kind of bizarre, because the hand felt painfully familiar, but Jimmy's hand had callouses in different places than Cas, but it also wasn't quite as strong-feeling. In fact, Dean had never noticed until now that Jimmy's hands were slightly more delicate, and found himself mesmerized as he absently stroked along the man's thumb and down to his wrist. Dean hated to admit it, but the handholding really was calming him down, and by the time the movie was starting, he'd mostly forgotten they were doing it.

The movie was captivating, and as with any good film, Dean lost himself in it easily, as he tended to do. The effects were awesome, the acting was fantastic, the characters were intriguing, and the plot was interesting, but not difficult to keep up with. All in all, Dean was enjoying himself, even during the heartfelt moments. Okay, maybe especially during the heartfelt moments, but no one had to know.

If he hadn't been so focused on the movie, he might have remembered that that wasn't Cas sitting next to him. But as it was, the body next to him felt like Cas, was holding his hand like Cas, and was nosing along his neck like Cas, so the sensory input seemed to be all Dean's brain needed at the moment to subconsciously identify the person next to him as his boyfriend. At the soft press of lips right below his ear, Dean sighed and slipped his hand over to the thigh next to his, without thinking. Cas always liked to get kind of touchy at the theater, so it was nothing unusual when he felt a hand slip up over his own thigh and palm at the bulge starting to form in his pants, as he felt flicker of tongue over his earlobe. And he probably would've kept on not noticing, if it hadn't been for the sharp nip of teeth right after.

Dean froze at the sensation, because that…was not a Cas thing to do. Cas' touches were always gentle until he got good and riled up, and oh. Right. Not Cas. As soon as the realization struck, Dean was leaning as far away as possible into his own seat, heart hammering as his focus was now entirely on Jimmy, who was giving him this little look of fond exasperation.

"Come back and let me tell you something," Jimmy finally said, beckoning him.

Dean didn't budge.

"Please, Dean."

It was the 'please' that did it, and reluctantly, Dean shifted so Jimmy could whisper in his ear, flinching a bit at the hand that came to rest on his thigh.

"You need to calm down, okay? Cas wanted us to have fun, that's why he sent me in his place; he's a good boy and knows how to share. I'll stop if you want, but Cas doesn't mind, alright?"

Dean shivered at the 'sharing' bit, unsure of whether Dean was the one being shared, or Jimmy. Both concepts were equally hot, and Dean blew out an unsteady breath through his nose. Of all the ways that Jimmy had messed with Dean over the months, this was nothing like any of them; Jimmy had never done anything that would hurt his brother, and Dean could see that the man wasn't kidding around. Somehow, he still had the presence of mind to form a very important question, despite the way the hand on his thigh was inching back toward his crotch.

"What uh… _shit_ ," Dean cursed, distracted as fingertips dipped down to trace along his balls. "The- _mmmm-_ " he broke off again, as that broad, hot palm pressed firmly against his crotch and a filthy chuckle sounded in his ear. "Goddammit, Jimmy, the password. What's the fucking password? Cas knows I'd want it." Even at a whisper, Dean knew his voice sounded strained, but couldn't find it in himself to be embarrassed because _Jimmy's_ _hand_ was on _Dean's dick_.

"I can't believe you two still use that stupid password thing. It's been like four months since I've really messed with you," Jimmy mused, a slight pout to his lips, and shaking his head. "But whatever. The magic word is 'meringue'."

Dean's brain promptly fuzzed at the confirmation and all he could do was stare at the hand rubbing at his dick for a moment in detached wonder, the movie all but forgotten.

"Want me to stop?" Jimmy asked, surprisingly gently.

"N-no, fuck no, but we need-," was all Dean got out, and then his body was working for him in the absence of words, rising from his seat and pulling Jimmy up with him. He reached for Jimmy's hand without a second thought and practically dragged him out of the movie complex, and over to the car. As soon as they were safely ensconced in the familiar comfort of the Impala, Dean turned in his seat to face Jimmy, who was mirroring his posture from his own seat with a look of curious anticipation.

After a pregnant silence, Jimmy finally took pity on Dean's wires still being a little crossed and prompted him.

"I'm guessing you have a couple of questions?"

A nervous laugh bubbled up Dean's throat. "No shit, man. Let's see. First, why don't we talk about the part where my freakin' boyfriend set me up on a date with his freakin' twin but was all vague about it, huh?" he said, gesturing wildly by the end.

Jimmy rolled his eyes to himself and let out a breath. "Dean, I'm gonna let you in a little secret. My brother? Not always so great at asking for what he wants, in case you haven't noticed. So let me ask you something. Ever get the sense that Cas might be kinkier than he lets on? As in, he's fine with it as long as you initiate it?"

Dean nodded, feeling the air get caught in his throat. This had to be what those people felt like right before the drama bomb was dropped on the kind of reality shows where someone's extensions end up getting pulled out during the season finale.

"So what if Cas maybe had a little voyeurism kink? Do you think he'd actually have the balls to say anything about it? He can barely even say the word 'cock' without his ears turning red," Jimmy said with a fond little grin to himself. "He cares about you a lot Dean, and doesn't want to scare you off, but the vanilla isn't cutting it. You turn me down, he doesn't really stand to lose anything. Well, he wouldn't if I hadn't told you all this," he said frowning at himself. "But anyway, I wouldn't have told you if I didn't think you were kinda freaky, yourself."

Dean took a moment to process this. "Soooo…Cas wants to watch me fuck someone else, and you…volunteered?" There was a lot more he wanted to say, but that was the first thing that came out.

"Not exactly. Cas wants to watch you and me. Specifically. And I agreed, because I'm a deviant and wouldn't mind see what all the fuss is about," Jimmy grinned, eyes roaming unapologetically over every inch of Dean he could see. "Of course, Cas is just as deviant, you know, or we wouldn't be having this conversation. You just have to know the right buttons to push with my brother."

"H-how much have you and Cas, um," Dean stumbled, feeling his face heat. Because this was definitely the million-dollar question that he'd been putting off for a long time now.

Jimmy just leaned over and turned the keys in the ignition, pausing to suck a brief, but harsh mark to the crook of Dean's neck before pulling back.

"I think you'd probably rather see, wouldn't you? So what do you say, Dean…are you down to fuck twins?" Jimmy asked, his smile saying that he already knew the answer.

Dean couldn't help the little whimper that escaped, and clamored to get his seat belt fastened. He looked to Jimmy, waiting on him to follow suit, but the man just shook his head.

"I think I'm just gonna stay put and keep this warm," he said, reaching over to rub a bold hand over Dean's erection. Again. "I trust your driving, Dean."

"You really shouldn't, if you're thinking about doing _that_ the whole drive back," Dean said, voice already going husky.

"It's either that, or listen to me say the dirtiest shit I can think of for the next fifteen minutes, from my side of the car," Jimmy grinned easily. "Either way, I intend on that cock staying interested til we can put it to use."

Dean blinked twice, slowly, and swallowed hard. "I guess I'll take the hand, then."

Jimmy grinned and batted his eyelashes. "I'm flattered that you think my mouth could be more hazardous than my hand, when you haven't even heard me before. Says a lot about what you think must go through my head." He punctuated the statement with a squeeze to Dean's shaft through the denim, and Dean inhaled sharply. "Hmmm. Looks like we have a lot to work with here. This will definitely be fun."

Dean huffed and put the car in drive and took off, needing desperately to get back to Cas and Jimmy's apartment, because he'd be damned if he came in his pants from a little bit of groping and an overactive imagination before the real fun could even begin.


	3. Chapter 3

Fortunately, for the safety of everyone on the road, Jimmy let up on all the palming and suggestive words as they made their way back to the apartment. He switched instead to teasing brushes of knuckles and the occasional single digit trailing up Dean's length as they drove and ludicrously, kept this up while discussing another movie that they'd all watched recently. Somehow it was more maddening, having that constant suggestion of what was to come, and not being enough touch to get lost in the sensation, it only served to encourage Dean's imagination to go completely wild with around six months' worth of ignored fantasies.

By the time they pulled up the apartment, a fine sheen of sweat had built up at Dean's hairline, and there was an uncomfortable wet patch steadily growing in his boxers. He hoped that Jimmy wouldn't notice the tremble his hands had taken as he reached to turn the ignition off, but one glance told Dean that he was shit out of luck on that one.

"See, that's wasn't so hard, now was it?" Jimmy asked with a cheesy grin, clearly pleased at his own obvious wording. "It was probably wise that you went with the hand, if this is how you are just after some light teasing," he said, affecting a look of mock empathy.

Dean shot him an half-hearted glare and hefted himself out of the car, Jimmy following suit. "You're still an assface," Dean grumbled, as they walked up to the apartment. Jimmy snickered, but didn't argue it.

The moment they made it through the door, Dean felt the last strings of his resolve snap now that they were in a safe space, and whirled around to yank Jimmy in roughly by his shirt. He paused, leaving a scant few inches between their faces and watched with satisfaction as wide blue eyes dilated, and Jimmy's tongue peaked out to wet his lips. _Not so cocky now, huh?_ Dean thought to himself. His pride must have shown on his face too clearly though, because that look of surprise transformed into a look of calculation as a smirk tugged at his lips.

"What're you waiting for, Winchester? Not quite sure what to do with me now that you have me?" Jimmy taunted, ending with a soft moan as he reached down to palm at his own erection. The little shit was doing everything he could to tease Dean, and had been for a few hours now and it was just as arousing as it was aggravating.

Dean smacked the man's hand away, replacing it with his own. "Oh, I know exactly what to do with this," he grinned. "But I'm sure Cas told you that, already."

Then Dean ran his hands around to grope at Jimmy's ass and pull their hips together, before leaning in for a filthy kiss. The first thing Dean noticed was that Jimmy tasted nothing like Cas, though there wasn't a definable taste that Dean could put to either twin. Jimmy was maybe…earthier? Compared to Cas, anyway. And whoa, what the hell did he just do with his tongue, holy shit! All thoughts of tastes and comparisons forgotten, Dean let himself get carried away by the force of nature that seemed to be Jimmy's tongue and groaned into the kiss.

They both needed more friction like yesterday, so Dean maneuvered them easily without breaking the kiss, to press Jimmy against the wall with a 'thump' and slip a thigh between his legs, grunting as he felt the answering erection press next to his own. Dean knew they hadn't exactly been quiet about it all, and wondered when Cas was going to make an appearance because he was definitely home; the twins' car was out front, and the door had been unlocked. The apartment was tiny, and it's not like you couldn't hear everything going on from any room in the place, so where the hell-

Jimmy broke the kiss and glanced over Dean's shoulder, before a sharp, fox-like smile took over his features that promised all kinds of dirtybad things. Dean knew on some level that that look could only mean that Cas was finally- _finally-_ in the room with them, but the shock of feeling his boyfriend suddenly pressing into his back while he was already pressed to another man had Dean freezing in place in a knee-jerk reaction. This had to be the definition of scared and horny.

But then Cas was sliding his hands under Dean's shirt to rub soothingly against his stomach and pressing gentle kisses to the side of Dean's neck. The gesture was just so sweet and so Cas, that Dean found himself calming instantly, relieved to finally have his boyfriend there with him.

"Jimmy must really like you, if he's letting you manhandle him around like that," Cas murmured against his neck, just jumping right in and not even bothering with his normal polite greeting. "That's not normally his M.O."

In a whoosh of air, Dean nearly emptied his lungs at hearing his boyfriend say such a thing, as if speaking from experience. _Holy shit, he is speaking from experience and Jimmy wasn't fucking kidding and oh my fucking god what the fuck is my life, JesusTapdancingChrist,_ Dean's thoughts jumbled, and he was pretty sure they broke down into non-syllabics for the next few seconds, as Jimmy tentatively rolled his hips into Dean's. Dean hadn't even realized that Jimmy had stopped moving when Cas came over, until then. A fresh wave of arousal washed over Dean, as the motion not only gave him some much-needed friction, but also rocked his ass back into the already-hard line of Cas' erection. Almost identical moans filled the air around him, and Dean shivered at the noise.

"What do you think, Cas? Still willing to share him with me?" Jimmy asked, head tilted so he could look at his brother over Dean's shoulder.

Cas rolled his hips tighter against Dean's ass, knowing it would press Dean's hips against Jimmy on the other side. Jimmy groaned quietly, and it only served to drive Cas on to do it a few more times, before tugging at Dean's hips in a silent request to turn around. Dean turned easily to face his boyfriend, unsurprised but very pleased when Jimmy crowded up behind him, now taking his own turn to rub up against Dean's ass.

"What do you think, Dean? I assume Jimmy has…enlightened you to a few things," Cas said, throwing an almost-unimpressed look over Dean's shoulder, at Jimmy. "Are you up for sharing? Yourself, and me? The three of us could have a lot of fun, and I wouldn't trust either of you with anyone else. Is- is this too strange for you?" Cas ended quietly, thumbs brushing over Dean's ribs where he'd rested his hands at Dean's waist. It was obvious that Cas wanted to look away in preparation for a rejection, but was willing himself to maintain eye contact.

Dean had to take a deep breath to try and think because by now, Jimmy had reached around Dean to grope at Cas' ass and rock him against Dean, while doing his own squirming against Dean's ass. Jimmy was sucking and nipping at the back of Dean's neck, while Cas was dipping his fingers into the back of Dean's waistband and pulling his collar aside so he could pepper little kisses across Dean's collarbone.

"I-I don't understand. You mean like all of us being boyfriends together or something?" Dean asked, a bit breathless under the twins' ministrations.

"Or something," Jimmy purred, then dipped to bite a little roughly at the crook of Dean's neck, pulling a surprised gasp from Dean. "We can work out the details later, but for now I think it's time we put on a little show for Cas. I think he's waited long enough." But then he hooked his chin over Dean's shoulder and was speaking to Cas, even as his hands wandered up to thumb at Dean's nipples underneath his shirt. "And Cas? If we're doing this, you should know that I won't go any easier on him just because he's your boyfriend. He can get his lovey shit from you."

Jimmy punctuated his statement with a surprising pinch to Dean's nipples that was just this side of painful, as if to prove his point, and turned his head to watch Dean's reaction. Dean realized a few things, then: for one, Jimmy was shaping out to be quite the toppy bastard; for two, that thought was much more enticing that Dean had expected, being kind of toppy himself, and three, Cas must've known that Dean wanted that on some level or he wouldn't have set this whole thing up to begin with. Well damn.

"I know. But judging by Dean's reaction," Cas said, glancing to Dean with a knowing little smile, "I think that suits all of us just fine. Am I incorrect, Dean?"

Dean shook his head, perhaps a bit more enthusiastically than he'd intended, and felt Jimmy huff a laugh against the back of his neck and shivered at the way it tickled.

"Not that we didn't need to get some of that out of the way, but for the love of all that is pure and holy, can we _PLEASE_ get naked, now?" Dean addressed the other two, collectively.

"There is nothing pure _or_ _holy_ about any of this, Dean," Cas grinned, shaking his head.

Jimmy snorted and pulled Dean's shirt off the rest of the way, from where it had been hiked up around his armpits, while Cas went in for Dean's pants, unbuckling his belt and releasing the button and zipper with practiced efficiency. He hadn't exactly been requesting that they team up to strip him, but Dean wasn't complaining, either. Jimmy grabbed him by the hips and twirled him around to face him once again and nudged him back a step. After an approving glance, he said, "Carry on, Cas. I just wanted to be able to see what you've been keeping to yourself all these months."

Cas obeyed, dipping his fingers underneath the waist of Dean's boxers at his hips and pushed the boxers and jeans down, all in one go until they got caught up at his ankles over the boots he was still wearing. Without prompting, Cas knelt down and removed his shoes and socks, and Dean rested a hand on Cas' shoulder to steady himself while stepping the rest of the way out of his clothes.

Now Dean wasn't body-shy by any means, but he couldn't imagine anyone _not_ feeling a little vulnerable under not one, but two sets of those soul-piercing blue eyes. Cas had come around to stand shoulder-to-shoulder with his brother, arms crossed over his chest, and looking over Dean with the kind of prideful admiration that clearly said, _'I did good…look at what I have. This is what I get to touch every night.'_

Jimmy's look was another thing entirely, though. He took his time, letting those clever blue eyes roam appreciatively at his own pace, and if he didn't know better, Dean would think that Jimmy was memorizing every individual skin cell. It was as unnerving as it was arousing, being devoured so thoroughly without even a touch, and Dean felt his face flush hot when his cock twitched noticeably as he glanced to the near-identical bulges in each man's pants in front of him. He was also then subjected to near-identical smirks, as both twins noticed exactly where Dean's eyes had roamed; it probably would've been creepy, if he weren't so turned on.

"You've been holding out on me, brother," Jimmy said, finally pulling his gaze away to look at Cas. Then he pushed off from the wall where he'd been leaning and circled Dean, as if admiring a car in a showroom, but infuriatingly, still not touching him. "Not that I can blame you, I don't know that I'd want to let this little secret out, either."

Cas just shrugged, a crooked grin settling on his lips as he winked at Dean when their eyes met. It was uncharacteristically charming, and Dean couldn't help the blush that rose to his cheeks. Not that Cas wasn't charming; that's just not the way that it normally manifested, and Dean was fascinated at the way his boyfriend seemed more confident and maybe even more…relaxed…in this new situation. It was beautiful, in a way, like watching a flower bloom.

"One more kiss before it's hands-off?" Jimmy asked Cas gently, nodding toward Dean.

Cas grinned softly and pushed off of the wall and stepped forward, reaching out to rest one hand on Dean's neck while the other came down to hook a couple of fingers around Dean's. When their lips met, Dean sighed into the sweet relief of Cas' familiarity, hands moving to rest at Cas' hips. The kiss was gentle and affectionate, the slide of their tongues unhurried as Dean relished what he could now identify as a sort of subdued sweetness to Cas' taste, in contrast to Jimmy's. Dean wanted to delve deeper, bury himself in it, but Cas clearly wasn't going to allow the kiss to become heated, subtly retreating his own tongue. After a few more seconds, he pulled back, stroking a thumb along Dean's pulse point.

"Sorry, but you know that would've kept going," Cas said with an apologetic grin.

"I think I'd like to see that, sometime," Jimmy drawled from next to them.

Dean startled a bit, having almost forgotten that he and Cas weren't alone, but such was life, kissing Cas; it had always been like that, the world falling away from Dean, under Cas' attention. When Dean looked over, Jimmy was giving them both that rare fond look now, but it fell away quickly as his eyes brightened again seconds later. Wordlessly, he grabbed Dean's other hand and led Dean and Cas behind him to his own room, where he had a queen bed; Cas only had a full-size, and they'd definitely need more room than that.

It was kind of weird being in Jimmy's room, as Dean had never gone farther than to poke his head in the doorway, and only a couple of times, at that. Where Cas' room was full of soft colors and a crisp masculine smell and generally orderly if not somewhat minimal, Jimmy's was the total opposite; his walls were a deep purple color, clothes strewn from one end to the other, the smell of incense lingering, and one wall covered in different sketches and paintings he'd done.

Cas let go of Dean's hand and walked over to flop down on a chair in the corner, where he had a perfect view of the bed. Jimmy led Dean to stand beside the bed and without further ado, started to undo the snap buttons at his shirt. The sound seemed loud in the quiet of the room, and with his ears drawn to the noise, Dean watched as long fingers worked the buttons, only then noticing the subtle tightness of Jimmy's hands. Oh god help him, Jimmy was actually a bit nervous, and Dean couldn't take that. Reaching out, Dean gently nudged Jimmy's hands away and proceeded to undress the man himself.

"Cas wants a show, so I think we should give him one. Whatcha say, Jimmy?" Dean purred, giving him a wink and what was hopefully an understanding grin. Gratitude flashed in Jimmy's eyes only briefly, but enough that Dean caught it and grinned wider.

Dean made a show of popping the buttons for Cas' sake, but the way his lower lip caught between his teeth at each new bit of skin revealed was all Dean. Jimmy shrugged the shirt off as soon as the last button was unsnapped, and Dean couldn't help but take a moment to stare, fascinated at the little differences between Cas and Jimmy. There were the same sinful hipbones and little trail of hair beneath his navel, same gorgeous collarbones and dusky nipples, but Jimmy's stomach was slightly softer-looking, and his skin was fairer; Cas was a runner, and tended to spend more time outdoors. Dean didn't bother resisting the urge to smooth his hands over Jimmy's chest and stomach, and was unsurprised to find that his skin was just as soft as Cas', though with a certain distinct smoothness to it.

Jimmy hadn't breathed a word, just letting Dean touch him as he pleased, but Dean got the sense that he was being indulged and moved on to unbutton Jimmy's jeans. When Dean pulled the zipper down, a little gasp escaped his own mouth that he tried to play off as a huff.

"Commando? Really? A little presumptuous there, huh?" Dean smirked. He heard Cas make a combination chuckle/choked off sound and glanced over to see Cas palming at himself and smirking at his brother.

"Please. I'm always commando, Dean," Jimmy leered.

Dean swallowed, and the 'oh' he'd been thinking ended up being said out loud. Both Novaks chuckled at that, but Dean ignored it and instead pushed Jimmy's jeans down, and stepped back so he give Jimmy a taste of his own medicine and stare at him as he kicked his jeans off. Apparently, Jimmy had no such qualms about his nudity, simply raising his arms above his head in a languid stretch, then bringing them down to rest on his hips proudly while Dean looked on.

Dean didn't know what to expect, but found himself unsurprised yet again, when he took in the fact that Jimmy's cock was basically the same as Cas', but curved more to his left. It was just as enticing, though, and Dean unconsciously licked his lips. He started to move forward, but Jimmy put a hand to Dean's shoulder and shook his head before turning to look at Cas.

"What do you want to see, Cas?" Jimmy asked his brother.

Cas had unbuttoned and unzipped his pants, but was still fully dressed and looked startled at being interrupted in the process of getting ready to pull his own cock out of his underwear. A blush rose to his cheeks as his hand froze at his waistband.

"I'm fine with whatever you two choose," Cas graveled quietly, glancing between Dean and Jimmy. When Cas saw that Dean was looking intently at his crotch, he started to pull at his waistband again, but Jimmy wasn't having it.

"No. Your dick stays in your pants until you tell us what you want," Jimmy said, mustering an authority in his tone that Dean had never heard before, voice dipping close to Cas' range. And god, if that wasn't one of the most attractive things Dean had seen.

Cas looked helplessly to his boyfriend, but Dean sensed that this was part of that button-pushing that Jimmy had talked about earlier, and just gave him an empathetic little half-smile. Cas pursed his lips and shot his brother a frustrated look that spoke of an old argument before releasing a sharp breath.

"I'd like to um…Dean, would you mind to," Cas broke off to clear his throat. "I'd like to see you put your mouth on him," he said, looking equal parts embarrassed and aroused as he spoke to his knees, before glancing back up to the other two men.

Dean smiled encouragingly at Cas, proud of him, but Jimmy didn't budge a muscle.

"I'm sorry, but whose mouth would you like to go where?" he asked Cas, eyebrow cocked. "And then what do you want it to do once it gets there?"

Cas glared at his brother, but it didn't seem to bother Jimmy in the least as he waited for his brother to reply. After a moment Cas cleared his throat before speaking, the words coming out in deep, irritated rumble at his brother.

"I would like for you to stay standing while Dean sucks your cock until you come."

That was the dirtiest thing Dean had ever heard his boyfriend say, and he'd be lying if he said he hadn't been wanting to hear Cas say something like that in his deep timbre, for months now. He couldn't help the little moan that escaped, and two sets of blue eyes locked on him simultaneously, one in surprise, the other in amusement.

"Looks like Dean would like that, too," Jimmy said, grinning wolfishly at Dean and winking. "But good job, Cas, I'm proud of you," he said then, voice a bit warmer. Cas grinned shyly, clearly proud of himself, too.

Stepping away from the bed, Jimmy moved to the wall next to Cas' chair and leaned back on it, a few feet away from Cas. "If I have to stay standing, I'm gonna need a little support, if your mouth is anywhere near as good as my brother's," he said, grinning at the way Dean gaped. "And he is good, isn't he? Talented tongue, that one," Jimmy said with a tilt of his head toward Cas.

Dean's feet moved before he'd made the decision, and suddenly, his vision was full of mirthful blue. He wasn't sure if he wanted to prove himself, or wipe that stupid smug look off of Jimmy's face, or both. Either way, Dean was hornier than he'd ever been in his life and done with this little game, and crashed his lips to Jimmy's in a clear sign that he'd had enough.

Jimmy opened for him easily, tongue immediately pushing out to tangle against Dean's. It was aggressive and dirty-sounding, and nothing like the way Dean and Cas ever kissed, the sounds of it filling the room. Dean had honestly thought until Jimmy implied otherwise, that Cas preferred the same gentleness that he always gave Dean, so Dean had never let it get too aggressive; passionate, yes, but not aggressive. But the way he heard Cas groan from next to them told Dean that he really needed to rethink that position.

Pulling away to breathe, Dean immediately set to attacking Jimmy's neck with licks and sucks, pleased as the man's hands came around to grasp at Dean's ass and pull him in tighter. Dean groaned around the skin in his mouth as their cocks came into contact, and Jimmy kneaded at his ass to pull him in for a deep grind, muttering his own curses. Dean worked his way down to Jimmy's collarbone, giving it the same treatment, nipping at the tender flesh next to the base of his throat.

"God _damn_ , Dean," he breathed, tip of an index finger skating over to dip at the top of Dean's crack. Dean gasped at the sensation, shuddering and moaning as the finger moved down to rub lightly over his hole. "Ever let Cas fuck you?"

"I've never asked to," Cas piped up, voice already half-way to wrecked.

"Oh my god, why?" Jimmy asked, disbelieving, looking between Dean and Cas with wide eyes.

Dean pulled back to look between the twins, slightly confused at Cas' somewhat guilty look. He was also surprised that Jimmy didn't know, considering what he'd said earlier about the twins discussing Dean and Cas' sex life.

"I don't mind bottoming for _Dean_ ," Cas muttered.

"You'd normally top?" Dean asked, eyebrows climbing at the revelation.

There was an awkward moment there, where Dean was pretty sure that maybe the three of them should have discussed all of this a little more, and Jimmy was looking between them with interest.

"Oh Dean, Cas can fuck like a machine," Jimmy supplied. "Jesus, Cas, you've been holding out on everyone. I mean, look at your boyfriend. Is this the face of a man that's uninterested in having your dick in his ass?" Jimmy asked, sliding his hand straight down Dean's crack, letting two fingers dip boldly between Dean's cheeks, causing Dean to groan- loudly- at the sensation.

Dean didn't care who topped or bottomed, but Cas had never shown any interest in topping, so Dean never bothered to push the issue. He's seeing now though, that maybe the two of them have a few things to discuss. Still though, Jimmy's hand was still rubbing insistently from perineum to the top of his crack, each pass pushing Dean's hips into Jimmy's in a slow grind, and the sensation and suggestion were putting Dean dangerously close to the edge. It certainly didn't help that Cas' eyes were impossibly dark and glued to the motion, as his hand started to stroke his cock faster, the head already leaking pre-come and making a slick sound.

Dean had to forcibly push himself back from Jimmy and collect himself because this was all so much more stimulating than he'd been prepared for.

"You," he said, pointing at Jimmy. "I'm going to suck your goddamned brains out through your dick until you can't remember what day it is while your fucking brother watches us. And you," he said, pointing at Cas, "had better be prepared because I fully intend on having every inch of your dick buried in my ass at some point in the next twenty four hours."

Cas gaped, but nodded, and Jimmy's breath hitched. Satisfied that that had all been cleared up, Dean nodded to himself. Then he dropped to his knees and worked two fingers in his own mouth, wetting them down before peering up at Jimmy. "Spread 'em," he ordered.

Jimmy looked surprised, and it dawned on Dean that the man had probably thought that Dean had meant to prep himself. But then he was acquiescing and spreading his legs apart, just enough to give Dean access while keeping himself supported.

Leaning in, Dean nuzzled and kissed his way up the inside of one thigh, and down the other, running slicked fingers behind Jimmy's balls to tease at his hole with a barely-there touch. God, how he loved these men's thighs. With that thought, Dean gave into the impulse he always tamped down with Cas, and bit down on the meat of Jimmy's thigh, hard enough to sting but not enough to leave a mark. It was more satisfying than Dean had expected, especially when it earned him a _'holy FUCK'_ , and he turned to give the other thigh a similar treatment, but finishing with series of nibbles up Jimmy's thigh until he reached the juncture of thigh and groin. Jimmy twined his fingers in Dean's hair, harsh little breaths sounding above Dean's head every few seconds.

Dean couldn't help but smirk as he felt the fingers tense in his hair as he scraped his teeth against the delicate flesh only a couple of inches away from the base of Jimmy's cock; he could easily imagine that Jimmy was concerned for the safety of his manhood with all the biteyness going on, but was choosing to trust that Dean wouldn't hurt him. The fingers relaxed their grip when Dean licked his way over until he could tilt his head and curl his tongue around the base, still only brushing a single digit over Jimmy's hole.

"Dammit, Dean, you're a fucking tease, you assface," Jimmy gritted out, using Dean's slur against him.

Dean chuckled as he licked a long stripe from base to tip, and without warning, swooped in take Jimmy's cock in his mouth, making sure to tongue the vein on the underside on his way down. With a startled grunt, Jimmy's hips bucked forward, but Dean anticipated and leaned back a bit to accommodate. Pulling out all his best tricks, Dean proceeded to take Jimmy apart with his mouth, pushing his finger in the man's hole in time with a particularly sinuous movement of his tongue around the crown of his dick.

One finger became two, as Dean mouthed at Jimmy's balls, sucking first one and then the other into his mouth. Jimmy's thighs were starting to tremble, as Dean's fingers crooked and stroked his inner walls, and Dean could hear Cas grunting and gasping right beside them. By this point, Jimmy was muttering nonsense and curses between panted breaths and moans.

_So fucking good, Dean…Jesus fuck…mmmm…god, Cas, gonna come?...gonna come watching your brother getting his cock sucked by your boyfriend?_

The dirty talk was definitely doing it for Dean, and his cock was achingly hard and steadily dripping pre-come down the length, begging for attention. Unable to resist any longer, he reached down to fist himself and moaned long and loud around the girth in his mouth, fucking Jimmy's ass with his fingers in time to his own strokes.

_God, you look so good like this, Dean…ah AH...shit…just like that…nnnng…_

Sure, Dean was good, but he realized belatedly that he wasn't _that_ good, as his rhythm was thrown off entirely as he tried to keep up with too many things at once; something needed to give. Dean took the opportunity to glance at Cas, and on an impulse, threw a wink his way before taking Jimmy all the way down, till the head bumped the back of his throat. Cas cursed under his breath and Jimmy let out a whine, and Dean could feel him starting to clench around his fingers and started to search in earnest for his prostate. They were all so close, and then…

_I can't…god, you're just a slut for it aren't you?...gonna lose it, Dean…_

Suddenly, Cas was out of his seat and right up in their space, leaning over Dean and in Jimmy's face.

"I'm not going to share if you're going to speak to him that way, I don't care how goddamned close you are. His participation is a gift, and you'll _remember_ that," Cas growled lowly at his brother.

Dean had never heard Cas sound so intimidating and serious, especially in reference to Dean, and could only blink upward from between the two men, Jimmy's cock slipping from his mouth as the man flinched backward slightly.

"Sorry, I didn't mean to-" Jimmy started to apologize, looking between Dean and Cas, but Cas cut him off to look down at Dean.

"Keep sucking him if you want Dean, but he doesn't deserve your fingers right now," Cas said, leveling a look on his brother at the end. Jimmy actually looked truly ashamed, and in an act of consolation, Dean reached up to run his fingers along Jimmy's length, almost petting him. Jimmy glanced down with an unreadable look, but Dean suspected that the man was trying to hold back a look of gratitude for fear of angering his brother even more. Not that Dean liked being called names like that necessarily, but it didn't offend him nearly as much as it apparently did, Cas. Things were tense in the un-fun way now, and Dean knew that he needed to do something that would appease all of them because this was going to be some major bullshit if the sexy times were ruined by a brotherly quarrel.

"Hey Cas?"

Cas looked down, anger draining from his eyes as blue met green, and carded gentle fingers through Dean's hair as they looked at each other.

"You know what I think?" Dean asked.

"Hmmm?"

"I think you two should kiss and make up," Dean said pointedly. "He said he was sorry."

Jimmy reached up now, and threaded his fingers in the hair at the back of Cas' head, scratching in an unexpectedly tender gesture and spoke softly.

"I don't like it when you're mad at me, Cas. You know I don't realize half the shit I'm saying when I'm all worked-"

Cas huffed a loud breath. "Yeah, I know. Now shut the hell up," he said, leaning in to kiss Jimmy much more fiercely than anything Dean had ever been on the receiving end of, and seconds later, Dean could hear the slickness of Cas starting to stroke himself behind him.

Dean's brain short-circuited at the sight above him; Cas, his gentle Cas, was kissing his goddamned twin like it was his fucking job to exact punishment in the form of tongue fucking. Jimmy shuddered and groaned, his cock freaking _leaping_ , just inches from Dean's face. Oh right, they'd kind of been in the middle of something a minute ago. Dean wasted no time, and went right back to sucking Jimmy's cock like he could pull the secrets of the universe out of the man's testicles, and started stroking himself again, too.

He could hear Cas and Jimmy kissing above him and it was about to be too much for Dean to handle because he couldn't look up, but he could hear Cas groaning now and Dean had no clue what Jimmy was doing to his brother. Dean was surrounded by those stupid Novak thighs and stupid Novak hips and he had no idea whose hand was in his hair, but someone was gently nudging his head back and forth on Jimmy's cock. Fuck, he was close, and by the way he had to hold on to Jimmy's hips to keep the man upright now, Jimmy was about to blow, too.

"Gonna come," Cas rasped, taking a step back, and out of Jimmy's reach. The hand also left Dean's hair, and he moaned as he realized that his boyfriend had been the one guiding him over Jimmy's cock. Jimmy echoed his moan, and Dean felt a blurt of pre-come spill over his tongue as the man's hips twitched in their effort not to thrust into Dean's mouth.

Dean blindly sought out Jimmy's hand and once he found it, placed it on the back of his head in encouragement. Frankly, Dean's jaw was tired and his lips were sore, and he needed to come and was ready for the end. Jimmy didn't hesitate at the offer and thrust in, fucking Dean's mouth in earnest.

Cas let out a throaty groan, followed by ' _OH MY FUCK,'_ and before the words were even all the way out, Dean could feel hot wet stripes painting his shoulders. Holy hell, Cas had never done anything like that, and Dean got one good moan in, before Jimmy finally lost it with one final thrust, coming hard down Dean's throat with a loud grunt _._ As soon as Dean was done swallowing around him, Jimmy pulled himself out and slid to the floor, his legs too loose to keep him up.

But then Dean was being tugged by his bicep in a request for him to turn around and face Cas, and fell back on his ass when he suddenly had a lapful of his boyfriend. Blessedly, Cas saw fit to finally kiss Dean with the sort of ferocity that he'd been frankly, jealous of, earlier. Dean moaned into the kiss as he realized that Cas was tasting _Jimmy's come_ in Dean's mouth, and then damned if he didn't feel Jimmy lean into him and start running his tongue over Dean's shoulders, cleaning Cas' come off of him. Dean's ears were practically ringing now, and when Jimmy reached around to close his hand over Dean's cock, that was all it took. Not even a single stroke, and Dean was coming harder than he could remember since the first time he had come inside of Cas without a condom.

Dean shuddered and shook with the aftershocks as Jimmy worked him through it, forehead thumping against Cas' chest, and Jimmy slumping forward to plaster himself against Dean's back. Cas carded gentle fingers through Dean's hair, and Dean wanted to wrap his arms around Cas' waist, but he was too boneless and breathless to move at the moment, so he settled for letting his hands rest on Cas' thighs.

It took several minutes for any of them to feel like moving, but eventually, Cas slid off of Dean's lap and slowly made his way upright. Jimmy was still draped lazily over Dean's back, and Cas toed at his brother's hip to get him to sit up. Cas held out both hands, and Dean and Jimmy each took one, grateful for the assist. After a hasty cleanup in the bathroom with too many elbows knocking, all three men trudged back to Jimmy's room and flopped down on the bed in a tangle of limbs, with Cas ending up in the middle.

Apparently, Jimmy was quite the post-coital cuddler; he immediately big-spooned himself in against Cas' back and wrapped arms and legs around Cas, and wedged a foot between the tangle of Cas' and Dean's legs. He even felt around until he found Dean's arm where it was tucked up between his and Cas' chests and wrapped his fingers around Dean's arm, right above his wrist. Even though none of them said a word, it was obvious that despite the stops and starts and bumps that night, in that moment between wakefulness and sleep, all three men were utterly content.

 

 

 

 

 

 

 


	4. Chapter 4

**Notes for the Chapter:**

> Ugh, I'm feeling schmoopy and gross about these three, don't look at me. Still though, hope you enjoy :)

"Mmmm."

Dean startled himself into wakefulness, when he realized that he'd been the one to make that sound; he didn't remember dozing off. Soft, warm lips were peppering little kisses over his back, and gentle fingers were tracing the lines of his back that lips couldn't reach. Cas. Dean sighed contentedly, enjoying the gentle attentions being lavished on him.

"Hey, Sleeping Beauty," Cas murmured affectionately.

"Hey, baby," Dean croaked, cracking an eye open in surprise at how rough his own voice sounded. Oh, right. A vigorous blowjob will kind of do that to you. Before he could even get as far as looking around, Dean heard Jimmy's voice lilting from the living room as he talked on the phone. He didn't bother questioning who the man would be talking to in what must be the middle of the night now; Jimmy was an unapologetic night owl.

Turning on his side to face Cas, Dean threw his arm over his boyfriend's waist and tangled their legs together. Cas hummed and drew in closer to press a kiss to Dean's forehead. They stayed wrapped up in each other like that for a minute, relishing the closeness. When they first started sleeping together- in both ways- Dean had put up token grumblings about all the snuggling, but Cas had ignored him because they both knew better. Dean fucking loved cuddling with Cas, dammit.

"How are you feeling? You know…" Cas asked hesitantly.

Dean knew what he was asking and sighed, knowing that he needed to answer honestly or this whole situation was going to get really convoluted.

"I don't know. It's kinda new territory for me, Cas. Don't get me wrong, that was hot as fuck, and I thoroughly enjoyed myself. But…what are we doing, exactly? Is this just a sex thing? Or are we all gonna be like together or something, or what?"

Cas sighed and traced idle patterns over Dean's chest as he considered his words. In the quiet, Dean noticed that Jimmy wasn't talking anymore, but he could hear the sound of the TV going.

"Actually, hang on a sec," Dean said. Then he covered Cas' exposed ear and hollered Jimmy's name. Seconds later, Jimmy appeared in the doorway, leaning against the doorjamb in a pair of flannel pants.

"You rang?"

Dean and Cas both sat up to lean against the headboard, and Dean patted the bed in front of him with a small smile. Jimmy padded over and sat on the side of the bed at a respectful distance. Dean's smile grew a little at the show of respect for the couple, even if it was kind of unnecessary, considering that Dean now knew what Jimmy's come tasted like.

"So what's the verdict?" Jimmy asked, looking between Dean and Cas with a carefully neutral expression.

"Nothin' yet. We were short a juror," Dean replied. When Jimmy just nodded and slouched a bit in his posture, Dean's eye was drawn to the line of the man's back. His mind wandered for a moment as he looked at the lines of muscle and knobs of spine and realized that he wanted to reach out and trace his fingertips along those lines.

Dean glanced to Cas then, taking in the shape of strong calves, and beautiful hands where they rested on his thighs, and on up to the little curl of hair behind Cas' ear. Dean couldn't help but glance to Jimmy again and grinned to himself as he noted the matching curl, as well as a cowlick on the crown of his head. Affection bloomed deep in Dean's chest for these two men, and he realized that Cas was looking at him curiously, a hesitant smile on his face.

"Can, um, you mind if…" Dean trailed off, eyes flicking to Jimmy before coming back to Cas. Despite the situation and the fact that Dean would freely snuggle with Cas these days, he still couldn't bring himself to outright ask permission to freakin' snuggle on Jimmy. If the man would even allow it, that is; he'd already proclaimed that the 'lovey shit' was Cas' job. Cas seemed to get what Dean was asking though and grinned softly as he nodded.

Jimmy had been watching them curiously, fascinated with the fact that he wasn't the only one that seemed to be able to communicate with Cas with minimal words. He honestly had no clue what the couple was communicating together at that moment, but he knew that it involved himself and stayed quiet as he waited.

"Jimmy will you just," Dean cut off, looking off to the side and flapping a hand in a somewhat beckoning gesture.

It seemed to Jimmy like Dean was indicating that he should draw closer, but he didn't want to move in case he'd misinterpreted. After a moment of more vague hand gestures and huffing and Jimmy's head tilting further and further as he looked between Dean and Cas, Cas finally had enough of the other two men and sighed dramatically.

"This is ridiculous and you're _both_ assfaces, by the way" Cas scoffed, rolling his eyes. "Jimmy, will you kindly get your ass up here and let Dean cuddle you, please?" When identical looks of offense and protest fell on Cas, he held a hand up and shook his head. "Just…don't. Dean, regardless of what you might call it in your head, the term for what you're wanting to do is 'cuddling'. And Jimmy, don't even start trying to act like you don't like it. And furthermore, Dean's good at it, so I suggest you take him up on it."

There was a moment of embarrassed silence as Dean and Jimmy tried and failed to hold eye contact and both of them twitched as if waiting for the other to make the first move. Cas groaned and rubbed his temples, wondering how the hell the three most emotionally constipated men in existence were going to pull this thing off; yeah, Cas knew he had his own issues, too.

Finally, Jimmy caved first, and scooted hesitantly toward Dean, not quite sure whether he was supposed to sit next to the man or lie down. Seeing the uncertainty in the normally confident man made something in Dean's resolve waver and he sighed as he accepted his fate. Scooting closer to Cas to make some room, Dean straightened his legs out in front of himself.

"Just…get over here and put your head in my lap, will ya?" Dean grumped at Jimmy. "On your stomach," he added.

Jimmy rolled his eyes, but acquiesced, lying down and turning his head so he could look up at Dean and Cas. When Dean weaved his fingers in Jimmy's hair and began to pet at him though, Jimmy's eyes fell shut immediately. He hummed a contented sound and then let out a deep breath when Dean's free hand moved to scratch lightly along his back, arching into the touch. Silently, Jimmy brought a hand up to rest next to his face and waggled his fingers in invitation. Dean was surprised at how endearing he found it and traded head-scratching duties with Cas, to hook a couple of fingers in Jimmy's.

The moment was peaceful and comfortable, and despite knowing how…unusual…it was, Dean knew then that he wanted whatever this was. None of them had said anything for a while, but Dean got the sense that the decision was mostly on his own shoulders and cleared his throat.

"So what are you two thinkin'? 'Cause I think I'm okay with whatever," Dean said, breaking the silence.

"I," Jimmy drawled, pulling the sound out, "think we should play it by ear and not worry about the feelsy stuff for now. You and Cas clearly have some things to clear up in the bedroom, so let's just look at this as sex therapy, and I get to be your helpful therapist," he said, rolling to his back and peering up at Dean and Cas with a smirk.

Dean liked the simplicity of that suggestion and gave a brief nod of agreement. But Cas looked chastened, even though Jimmy hadn't implied any sort of judgment on them, and Jimmy rolled his eyes at his brother. Sure, Cas may have been keeping a lot of things to himself, but it's not that uncommon for people to feel uncomfortable letting their partners know what they want in bed.

"Stop that," Jimmy said, reaching a hand above his head to knock his knuckles against Cas' thigh. Cas looked even further chastened at that, but nodded and leaned his head on Dean's shoulder.

"I like this part," Cas admitted quietly, pointing between the three of them.

Dean couldn't help but grin at his sweet- and now confirmed secretly kinky- boyfriend and turned his head to press a kiss to the top of his head. Jimmy seemed to recognize the couple-y moment for what it was and looked away, a little grin resting on his own lips because dammit, Dean and Cas were fucking adorable, and he couldn't _not_ see it. Still though, he felt the need to confirm what was going on because frankly, he was piled up in the bed with two naked men and had a job to do. A quiet cackle escaped his lips at his own mental double-entendre and he felt two pairs of eyes zero in on him curiously.

"Nothin' guys, don't worry 'bout it," Jimmy said, another snicker slipping out before he composed himself. "Right. So I'm gathering that the three of us are going to have all the sex, and if any combination of us maybe needs some PG-13 love'ins from time to time, that's okay too. I'm also assuming we'll all just carry on as we always have in public. All of that sound about right?"

Dean and Cas looked to each and seemed to have one of those silent married-couple conversations for a second that ended in Dean nodding, before Jimmy and Cas had one of their own.

Regardless of the rather basic way that Jimmy had laid it out there, Cas could see the underlying concern in his brother's eyes, as he silently looked for any sign of hesitation on Cas' part. Jimmy had always been full of bravado and often times didn't seem to shut up when he probably should, but when it came down to it, Cas knew that Jimmy would never do anything that could possibly hurt him, including help destroy a relationship. That show of concern made affection flow like warm honey under Cas' skin and he couldn't help but reach out to card his finger through Jimmy's hair because the man's heart was as big as his mouth.

"I think that's the gist, and we'll just play it by ear, as you said," Cas said with a small grin.

Dean then found two pairs of blue eyes blinking at him, and realized that they were waiting for his final approval. "Uh, yeah. Sounds good to me," he shrugged, ending with a yawn.

And with that yawn, it became obvious that now that the important stuff was out of the way and they could all relax, no dicks were going near any orifices for the rest of the night. But it was okay, because they had time for that tomorrow.

"Can we all just stay in here tonight?" Cas asked the other two, scratching lazily at his chest. "I'm comfy and don't wanna move."

Jimmy just made a non-committal 'meh' kind of sound and squirmed his hips to get his pants off. "I don't care, as long as I'm not in the middle, being all crowded in by you two." And then his naked ass was wriggling over to Dean's other side and grabbing for the blankets. "And I don’t do the little spoon, either," he added, giving Dean a look that dared him to argue.

"He gets claustrophobic," Cas explained.

Dean chuckled a little bit as he and Cas both worked to get themselves under the covers as well.

"Yeah, I know. Thought he might've been full of shit earlier, though," Dean smirked.

"Oh?" Cas asked curiously, arranging himself to drape over Dean and lay his head on Dean's chest, and tangling their legs together.

Jimmy had his back to the other two, but waved a hand in the air, as if he just assumed they were looking at him. "Pffft…I wouldn't let an armrest stop me from feeling you up, Dean. S'easier without it there, but not impossible," he said, sleepiness coloring his voice now.

Cas snorted, his grin making the stubble on his face shift and scrape against Dean's skin. "That's true," he agreed.

Dean flicked Cas on the arm with one hand and Jimmy on the back with the other. "You two need to shut the hell up right the fuck now because you're putting all kinds of images in my head that I'm too tired to do anything about right now."

Matching dark chuckles sounded on each side of him, and Dean heaved a great sigh. "You're _both_ little shits when you want to be," he grumbled.

Jimmy scooted his ass back to rub playfully against Dean's hip and Cas laughed at Dean's second great sigh as his boyfriend no doubt wondered what he'd gotten himself into.

 

* * *

 

For the second time in 24 hours, Dean woke up to being touched, though this time the touch wasn't quite so innocent. As usual, he'd rolled to his stomach in his sleep, and warm hands were kneading at his asscheeks. He hummed deep in his throat, but didn't bother opening his eyes, still hazy and only half-awake and content. But then there was a tongue pressing at the very top of his crack and well. Dean was fine with wherever this was going, especially when those hands moved to his hips, directing him to get his knees under him. Cas was always kind of frisky in the mornings, and Dean grinned to himself, pillowing his forehead on his arms.

At the tell tale scrape of stubble against his asscheek, Dean's breath hitched, and then blew out harshly as he felt the first tentative swipe of tongue against his hole. The attention was careful and deliberate, working him up slowly, perfectly, as he became more and more awake. But then a clever swirl proceeded by the tip of that tongue working past the rim had him moaning, and he was definitely fully conscious then.

"Cas," Dean breathed, hips pushing back in encouragement.

A dirty chuckle against the sensitive skin vibrated through him, and Dean shivered.

"Try again."

At those two words and in the wrong voice, Dean's head whipped so fast over his shoulder, something popped in his neck. "Holy shit!" he gasped.

Jimmy had settled back on his heels and was grinning wickedly, lips spit-slick, and hands still on Dean's ass as one thumb brushed teasing close to where he'd been working. Still so aroused, and especially by the sight of fucking _Jimmy_ looking so pleased with himself, it took Dean's brain a second to catch up, and then he shooting upward to sit. When Dean was finally able to bring his eyes to the other man, Jimmy was giving him a wry smile.

"I know it's not my skill that has you skittering off, so I'm guessing you're freaking out because it's me," Jimmy said, sighing with a half-smile. "Cas is taking a shower and told me I could get you ready for him, if I wanted."

Dean blinked at Jimmy, then his eyes shifted to see the little bottle of lube sitting innocuously off to the side on the bed.

"So, are you gonna get your ass back down here? Cas woke up in a mood, and I'm inclined to indulge him, if you still are," Jimmy said, putting emphasis on 'mood'.

Dean's ears perked up at that, because hell yeah, he wanted to see Cas in a 'mood'. "Yeah, just…give me a minute. I'm gonna need to take a piss first if we're getting into all this first thing."

Jimmy gave a grand 'by all means' gesture toward the bedroom door, and Dean walked out to the kitchen. He hadn't been lying about needing to pee, and needed his erection to go down pronto, so he grabbed a beer out of the fridge and wrapped it in a paper towel before holding it painstakingly to his groin. It might not have been the most comfortable method, but the cold did its job, and soon he was slipping into the bathroom.

"Just me," Dean muttered in warning to Cas, not wanting to startle him.

Cas grunted an acknowledgement and waited until it sounded like Dean was done before poking his head around the curtain. He looked at Dean with a confused frown.

"Are you okay? Don’t take this the wrong way, but you should be hard and moaning by now," Cas said, eyebrows scrunched.

Dean snorted and leaned in to kiss Cas on his wet forehead. "Yeah, well, that was before I realized it wasn't you and that you're apparently impatient enough that you wanted to be able to…slide right in to the good stuff," he said with a grin. "Figured I'd better pee first."

Cas had the good grace to look a little embarrassed at being called out, but not necessarily about the truth in Dean's words. "Sorry. I'm just really…Dean, I'd really like to fuck you, if that's still an offer. I know we have a bit to talk about, but suffice it say that I've wanted you in every way imaginable for a long time now," he confessed.

It might not have been dirty talk, but it still sent Dean's cock twitching in agreement, nonetheless. "Well, you've got me. And we'll talk later, but for now I think it best if I get back in there and get ready so you can show me what those thighs can really do," he said with a wink.

Cas opened and closed his mouth a few times, before finally settling on a nod and a crooked grin. Dean leaned in for a quick kiss, but before he pulled away completely, had one more thing to add. "Also, I expect some dirty talk, if we're making up for lost time here. Am I wrong that that's another thing you've been holding out on me?"

Cas blushed, looking guilty. "I've only ever done that with Jimmy, and not very much."

"Well, then I guess I'll just have to make it good enough that you can't keep it in," Dean purred, stroking a thumb over Cas' lower lip, and feeling pleased at the hungry look that had crept into Cas' eyes.

And with that he turned around and went back to the bedroom, where Jimmy was stretched out on his stomach and flipping through an old Rolling Stone on the bed. When Dean stepped closer, his eyes couldn't help but zoom in on Jimmy's ass.

"Oh my god," Dean breathed.

"It's only been like five minutes. I seriously doubt I look any better than I did when you walked out," Jimmy teased, tossing the magazine to the floor.

Dean huffed and pointed at Jimmy's ass. "Are you wearing a plug?"

Jimmy's eyebrows raised and he glanced over his own shoulder as if he'd nearly forgotten, then shrugged. "Why not? You're not the only one expecting some action today."

Jesus, these men were going to be the death of Dean Winchester.

Without a good response to that, and knowing that one wasn't really needed, Dean let himself give in to the whole situation and grinned as he sat down on the bed.

"How do you want me?" Dean finally asked, quirking a flirtatious brow; he liked flirting with Jimmy, and with permission to do it now, Dean was going to enjoy the benefits, dammit.

Jimmy's eyes flashed darkly as that fox-smile pulled at his lips, and he sat up. "Oh Dean, I don't think you're ready for me to answer that honestly, but we'll get there. For now though, as you were before." Then he seemed to think of something and his face turned more serious. "How long has it been since you've had anything more than a tongue in your ass?"

Dean felt his face flush, stupidly, considering what they'd already done, but it was still kind of weird having to share something so personal with his friend. He knew why Jimmy was asking though, and appreciated the thoughtfulness.

"Um…about a month? Just my fingers, though," Dean replied, staring with feigned interest at the pattern on the sheets.

Jimmy sighed in frustration, shaking his head. "For such a smart guy, my brother can be fucking clueless," he muttered, reaching for Dean's hips and pulling him down the bed as if they'd done this a million times. "Not anymore, though. We're gonna take good care of you, Dean."

Dean got the sense that Jimmy hadn't meant for the words to come out as affectionately as they did, when Jimmy's eyes darted away as soon as he'd said them. That warm feeling bubbled up in Dean's chest, but he didn't dare make the moment into more of a chick-flick, opting instead to spread his legs a bit in invitation with a teasing little smile. That brought Jimmy's more familiar smile back to his face, and Dean mentally congratulated himself for navigating that heartfelt moment successfully, when Jimmy gave a satisfied nod.

"Alright then. I'm gonna make you feel good, Dean, but you aren't allowed to come. Understood?" Jimmy asked, that authoritative tone that Dean had heard the night before seeping in.

No one had ever just told Dean what to do in regard to sexy times like that, and though his first reaction was to argue, he was also kind of intrigued. This was supposed to be about trying new things, after all.

"Fine," Dean agreed, somewhat reluctantly.

Jimmy grinned and patted his thigh. "Good. On your knees, then. I want that ass up in the air for me."

Dean squirmed back into position, feeling a hell of a lot more exposed now than he did earlier; Cas may have spent plenty of time back there, but this was Jimmy, and Dean felt a sudden urge to hide in his self-consciousness now that he _knew_ who was behind him. But then those warm hands were palming at his cheeks again, and Dean heard a pleased hum.

"You know you've got a really great ass, right?" Jimmy asked, before pressing a kiss to Dean's tailbone. "Nothing to be ashamed of, so just relax, okay?"

Without waiting for a response, Jimmy dragged the flat of his tongue from Dean's sac to hole with a perfect pressure that had Dean letting out a moan, and all thoughts of self-consciousness falling away. The man's tongue was every bit as wicked as he'd let on, and within minutes, Dean was fully hard and panting as Jimmy's tongue plunged deep, then retreated to flick teasingly at the rim before repeating the motion. It all felt so much like Cas, but at the same time, exhilaratingly different. Dean gasped when a single, graceful digit slid in, his breath shuddering as he released it.

After a moment, Jimmy's tongue rejoined the action, and he hummed a pleased sound at the way Dean's body relaxed to accommodate the extra thickness. When Dean's hips started to twitch back in little aborted movements, Jimmy pulled his mouth back and reached for the lube, anticipating.

"More?" He asked.

"God, yes," Dean husked, pushing back encouragingly.

Wasting no time, Jimmy pulled his finger out and drizzled some lube on two fingers, warming it up for a moment and then rubbing it over Dean's hole in warning before pressing in slowly. When Dean tensed and hissed at the burn, Jimmy reached with his free hand to stroke Dean's cock, but didn't stop the slow drag of his fingers.

"You're doing so good, Dean, especially for being so tight," Jimmy said calmly.

Dean was surprised at how careful Jimmy was being with him, and though he appreciated the thought and warmed more at the praise than he cared to think about, he also kind of wanted to move this along.

"Well, then let's fix that, hmmm?" Dean said impatiently, as he pushed his hips back.

Jimmy huffed a laugh and immediately moved his fingers to start scissoring, earning a gasp, then a moan as the tip of a finger brushed against Dean's prostate a second later.

"Wasn't expecting to find that so quickly," Jimmy commented, then repeated the action, chuckling at the way Dean bucked his hips back and groaned. He made it a point to avoid touching it again though, and began opening Dean up in earnest when he heard the water shut off as Cas finished his shower.

Dean groaned in combined frustration and arousal, at the way Jimmy was purposely ignoring his prostate, completely in control of how much pleasure Dean received at the moment. When Dean swiveled his hips in an effort to get those nimble fingers where he wanted, he was stunned as he received a short smack to his ass for it. He glared over his shoulder at Jimmy, but the man just shook his head.

"No," Jimmy said, voice pitching low. "I'm not going to make you come, not yet. Your first orgasm of the day is going to be from Cas' dick, and nothing less."

Dean sighed and lowered his head back down to his arms in a gesture of acquiesce and was rewarded when Jimmy started moving his hand again. After a moment, the stretching started back up, and Dean was getting ansty. As if reading his thoughts- or more likely, his body- Jimmy pulled his hand away to drizzle more lube and then was back with three fingers.

It still burned, but Dean couldn't help but moan at the fullness, knowing that soon he was going to have Cas inside him. Soon, the burn was replaced by pleasure, as Jimmy worked him into a frenzy, not bothering to chide Dean for rocking back on his hand seeking more. Curses and moans were falling from his lips, and occasionally Jimmy's, and pre-come was now steadily leaking from Dean's cock; it was probably a good thing that Jimmy hadn't touched it in several minutes.

"I taught him well, didn't I?"

Dean tensed in surprise at the sudden rumble of Cas' voice from behind him, and Jimmy cursed as Dean unintentionally clamped down on his fingers.

"Fuckin' hell, Cas," Jimmy whined. Dean felt a touch of satisfaction that even Cas' own twin wasn't invulnerable to his ability to sneak up silently. "And you should know that your boyfriend's ass might break your dick, by the way," he said, absently stroking Dean's spine and trying to get him to relax.

"What the hell were you doing in there for so long?" Dean asked Cas, then smiled hastily at Jimmy, hoping he understood that it wasn't a complaint against him. Jimmy didn't seem offended though, and just went back to what he'd been doing, drawing an embarrassing mewl from Dean. "And _what_ did you say?" he asked his boyfriend breathlessly.

Cas came around then, and sat down next to Dean's elbow, cock already completely hard and less than a foot from Dean's face. He wanted to reach over and touch it, but that would require moving too much, and Jimmy's hand felt _really_ good exactly where it was.

"I figured I'd take my time, since I knew that Jimmy would with you because as I said, I do believe I taught him well," Cas repeatedly boldly.

Dean moaned at the filthy imagery that popped into his head in time with a purposeful stroke against his neglected prostate.

"You fucker," Dean panted, with a half-hearted attempt at a glare over his shoulder. Jimmy just smirked and did it again, before pulling his hand out slowly and glancing to his brother.

"You want him any looser, you'll have to do it yourself. I need a minute," Jimmy said, flexing his fingers and nodding down pointedly at his own neglected cock.

Cas actually snickered at that, but nodded and moved to take Jimmy's place behind Dean. The click of the lube cap sounded, and then seconds later, two slick, gentle fingers were sliding into Dean. He moaned quietly as Cas worked them in and out a couple of times, relishing the feeling, because so far Cas had only ever fingered him a couple times, and the man definitely knew what he was doing. Soon after, two fingers easily became three, and Dean squirmed, trying to get more than just the gentle prodding he was receiving.

"Come on, baby," Dean encouraged, though it came out a bit whiny, even to his own ears.

"You're still kind of tight, Dean," Cas said, spreading his fingers on the way out. "I know I'm not enormous or anything, but I also don't want to hurt you and would feel better if you'd take a fourth finger."

Oh, fuck that. This was going to take forever, and Dean just didn't have the patience anymore. The moment Cas withdrew his hand, Dean pulled himself up to kneel and in a flash had manhandled Cas around until the man was lying on his back with Dean straddling his hips. Jimmy outright laughed at the wide-eyed surprise on Cas' face and 'oh shit' that slipped his lips. Dean couldn't help but grin, himself, and leaned down kiss the look off of his boyfriend's face.

"Baby, I love that you want to take such good care of me, but I'm not made of glass," Dean said, holding a hand out in Jimmy's general direction. The lube appeared in his palm right after, and he spared a glance to grin gratefully at Jimmy for understanding, before turning back to Cas. "I'll even take the pressure off of you and do this part myself."

And then he was slicking up Cas' cock and applying a little more to himself, before maneuvering into place.

"Dean, I don't think you should," Cas began, clearly still worried, but then cut off with a moan when Jimmy reached over and guided Cas' cock to rub the head along the full length of Dean's crack.

Dean grinned around a quiet moan and looked to Jimmy, giving a small nod. Then the smooth, round head of Cas' cock was right there, nudging gently at Dean's hole, and he sank down slowly, ignoring the burn as it fully breached his rim.

Cas gasped and shuddered, hands coming up to grip at Dean's thighs as he made a controlled effort not to move and let Dean adjust on his own. And it was true that maybe Dean should've taken that fourth finger, because Cas' dick in his hand or mouth felt nowhere near as big as the length now starting to fill him. As he slid down just a tiny bit more, Cas began to pant furiously, and Dean looked down in time to see Jimmy's hand squeeze harshly at the base of Cas' cock.

"That's cheating," Dean tsked. "If Cas thinks he can handle my ass, then he's gotta be a big boy and control himself without help."

Jimmy snorted and shrugged and removed his hand, scooting off to the side to watch. Cas looked at his brother pleadingly, but Jimmy's grin just widened as he shook his head. Cas looked up to Dean, eyes wide and dark, and clearly overwhelmed at the sensation of being inside someone after so many months without. In that moment, Dean felt powerful, much more than he ever did when pushing himself into Cas, and couldn't help the satisfaction that curled his lips.

Another agonizingly slow minute later, and Dean was fully seated and blew out a deep breath as he waited for his body to finish adjusting. Cas had had to close his eyes by now and take calming breaths, fingers twitching restlessly at Dean's hips. It was actually endearing, and Dean leaned forward carefully so as not to dislodge Cas' cock, and pressed a gentle kiss to Cas' lips, swallowing the small gasp his movement had elicited.

"You good, or you still need a minute?" Dean asked, kissing the corner of Cas' mouth.

Cas nodded shakily with a raspy, "I'm good," giving Dean's hips a gentle squeeze.

Dean drew back up and grinned wickedly. "Glad to hear it, 'cause I'm 'bout to show you exactly why you shouldn't keep what you want from me."

And with that, Dean rolled his hips in a sinuous movement to start them off and both men moaned at the sensation. A few more rolls, and then Dean lifted up and slammed back down, impaling himself on Cas' dick, squirming his hips as he bottomed out again. Cas looked like the breath had been punched out of him, and Dean repeated the action, chest filling with pride that he was able to give this to his boyfriend. Cas started to meet him thrust for thrust as the pace picked up, and before long, something seemed to snap in Cas as a wild look came into his eyes that Dean was nearly stunned by.

Cas suddenly pulled his knees up to plant his feet on the bed, and with a near-painful grip on Dean's hips, pulled Dean down as he thrust up with his improved leverage.

"Holy shit!" Dean gasped. And then Cas was looking really pleased with himself at the reaction, and Dean didn't know that he'd ever been so turned on by a look in his life.

Dean may have been on top at the moment, but there was no mistaking that Cas was the one steering this ride, and Dean was glad to let the man take what he wanted as those powerful thighs and hips pumped so beautifully. He could see now what Jimmy had meant, and glanced over to see Jimmy unashamedly stroking his own cock with one hand, while the other pumped his fingers in and out of his own hole, plug removed and tossed to the side. When Dean realized Jimmy was working himself in time to Dean and Cas' rhythm, Dean groaned a loud, 'oh my GOD'.

Cas looked over then too, and glanced between Dean and Jimmy, slowing the rhythm of his hips. Dean knew what Cas was thinking and had to squeeze the base of his cock.

"Don't stop on account of me," Jimmy said, voice rough and eyes feverish with arousal.

Dean leaned down to place a rough kiss to Cas' lips and as he pulled away, he nodded. Cas grinned crookedly and released Dean's hips so he could slide off of Cas and turn to Jimmy.

"I think you should get on your hands and knees, now," Dean said, eyebrow cocked. At Jimmy's only slightly guarded hopeful look, Dean grinned and shrugged. "Unless you're having too much fun rocking your own world over here."

Without any more hesitation, Jimmy moved quickly into position. Dean chuckled and grabbed the lube to slick himself up and added more to what Jimmy had already used. He pushed in slowly, despite the fact that Jimmy had already worked himself pretty well open, and cursed as the tight, wet heat enveloped him.

"Christ, Jimmy. Didn't think you'd be so eager, but look at you, ass practically swallowing my dick. How long've you been wanting me to fuck you, hmmm?" Dean asked, as he waited to make sure the man was okay. "Thought it would've been the other way around, honestly," Dean admitted, running a soothing hand up Jimmy's flank.

Jimmy groaned and hung his head, shuddering a bit. "Don’t be a shit, Dean. Pleasure is pleasure and I'm man enough to admit that I don't mind a dick in my ass on occasion." He punctuated this by giving a tentative push back and letting out a shaky breath. "And if you must know, since we saw you grinding on that guy at that party. "

"Oh my god. I thought I imagined that I'd seen you two there," Dean said, face flushing. "It's still kind of hazy."

Jimmy huffed and pushed back again. "No, we definitely saw it. And then we went home and jerked off together, talking about what you'd be like in bed."

Dean released a ragged moan and pulled Jimmy's hips to him in a short sharp thrust, not even caring that the man was trying to egg him on to moving. It worked, and Dean was rewarded with a loud grunt, and then a _fuck, Dean, just like that…come on, fuck me like you mean it…_

And then Dean was fucking into Jimmy in earnest, relishing the seemingly endless string of curses and groans he was earning as he snapped his hips mercilessly into the younger Novak. After a minute, he could feel the way Jimmy was getting close and slowed down to an eventual stop, because it wasn't time yet.

"Get over here," Dean said to Cas with a tip of his head as a beckon.

Dean draped himself over Jimmy's back and pressed calming kisses to his neck as he waited for Cas to crawl over and get in position, knowing that Cas would do it. Soon enough, Dean felt the heat of Cas' body behind him, and then the blunt head of his cock pressing in again as a broad palm held Dean's hips in place. He groaned, but stayed still as he was overwhelmed by the sensation of both filling and being filled; the rhythm could get tricky here, so he decided to let Cas start the pace. A moment later he did just that, pulling out and then shoving back in with one long, deep thrust that naturally served to push Dean into grinding more deeply into Jimmy.

All three men groaned, loudly, and then in a chain reaction, Cas pulled back so Dean could too, and then they slowly started got into a rhythm. It took a minute, but once they found the magic rhythm it was incredible, and nothing that Dean could've been prepared for, every pull away from Jimmy's body pushing himself onto Cas. It was sweaty and noisy and frantic, and Dean was easily swept into the push and pull as both of the Novaks gave and took, keeping him close as they all chased their own release.

Dean knew that this couldn't last long, and could feel himself approaching the end at a startlingly fast pace, and told the other two as much. Cas picked up the pace, pounding hard and fast, rhythm starting to falter and then Jimmy started to clench around Dean, whose voice went high with noises he hadn't known he could make.

"Now! Fucking now…harder, Cas!" Jimmy shouted.

Dutifully, Cas put everything he had into it, practically shoving Dean into Jimmy, and then the man was coming with a loud 'AAGH', his ass clamping down shockingly hard on Dean's cock. That was all it took, and with one final thrust from Cas, Dean was coming hard, eyes rolling in the back of his head as he spilled into Jimmy without a sound; he couldn't make sound, it wasn't possible. It was just too much, especially as he felt Cas pulse inside of him as he followed Dean right over the edge, come painting his insides hotly.

There seemed to be a moment there where time slowed down, as Dean tried to regain his breath, not sure if it just him that was trembling, or if all of them had just had their minds blown so thoroughly. Then it all came crashing back as Cas pulled out, and then Dean and Jimmy were collapsing together on the bed, onto their sides. Jimmy didn't even complain that Dean was still wrapped around him and holding on for dear life, as if he'd float away into space if he let go.

Cas flopped down behind Dean then, and all that could be heard for the next few minutes was the sound of harsh breaths as they all recovered without a word. Dean was eventually able to peel himself away from Jimmy, and rolled to his back, letting out a shuddering breath as he looked over to Cas. Cas' eyes were nearly glazed over, and an awed smile was plastered on his face. His hair was a mess and the color was still high in his cheeks from exertion, but Dean had never found him so beautiful and felt himself puff with pride that he'd been the one to bring that look to Cas' face.

Jimmy rolled over then, too, not looking much better, and Dean couldn't help but wonder if his own face looked so completely fucked out. Oh, who was he kidding? There was no way he didn't have the same look. His mouth was moving before he'd planned on saying anything, and it showed in the words that tumbled out.

"That was…I can't even…holy…" Dean babbled, trailing off with a sigh. "Fuckin' A," he finally croaked, giving up entirely on speech.

Jimmy chuckled and reached across Dean to find Cas' hand and lace their fingers together over Dean's stomach.

"I think we broke him," Jimmy grinned, still chuckling.

Cas snorted and leaned in to nuzzle at Dean's temple before dropping a sloppy kiss there, then seemed to decide at the last second that that wasn't enough and proceeded to pepper his face with little kisses, laughing quietly to himself between pecks.

"You gonna be okay?" Cas asked teasingly, when Dean didn't even seem to have the wherewithal to try and kiss him back and just accepted the affectionate assault.

Dean swallowed harshly around a dry throat and turned his eyes to Cas.

"Yeah, I um…I just. Christ, I wasn't prepared for that. Have you two done that before?" Dean asked, looking between the twins.

Jimmy shook his head, an amused little grin on his face. "No, not together."

"We've never had a third person," Cas chimed in. "And I've never had a threesome at all."

Dean turned to look at Jimmy expectantly, who just shrugged and smirked.

"Jimmy had twins once, though; two girls," Cas supplied.

Dean sat up at that and looked at the other two men, Cas grinning wryly and Jimmy looking utterly amused at the memory.

"You've got to be shitting me," Dean said flatly. When Jimmy only cocked an eyebrow, Cas snorted, and then laughter was bubbling up Dean's throat and spilling out. "Oh my god, that is ridiculous."

Jimmy's grin stretched wider and he couldn't help but laugh, himself.

They all sobered for a minute, somehow ending up in a tangle of limbs again without really realizing they'd done it. Dean released a long, contented sigh as he stared at a hairline crack in the ceiling, mind wandering aimlessly as the exertion caught up with him. But then something occurred to him.

"You still owe me some dirty talk," he blurted, turning his head to look at Cas. "And I know it had nothing to with me not making it good enough," he smirked, referring back to his earlier tease in the bathroom.

Cas grinned a little bashfully, which should have been ridiculous all things considered, but Dean could only feel endeared at seeing the familiar look.

"No, you definitely made it good enough," Cas agreed, still grinning. "But I promise I'll work on it. I might need some more encouragement, though," he said, batting his eyelashes.

Dean snorted, and Jimmy breathed a 'oh good god', as he sat up, claiming that he needed to pee and muttering about 'lovey shit' and 'too early for this crap' as he walked out of the room. Dean didn't miss the way a fond grin was battling to make itself known on the man's lips though.

This would've been the perfect time for Dean to say something witty or flirty or even offer a 'thanks for trusting me', but nothing was coming to mind that seemed sufficient. The way Cas was looking at him like he'd hung the moon though, told him that Cas understood, and the smiley kiss he laid to Dean's mouth only confirmed it. There would be plenty of opportunity for them to work on their communication issues, but for now, it was time to just enjoy the afterglow.

"If you're done being all gross and couple-y, there's coffee going," Jimmy's voice filtered in from the kitchen, teasing and warm.

Dean chuckled as Cas rolled his eyes because yeah, he could definitely get used to this. 

 

**Author's Note:**

> Come give me a holler on my [Tumblr](http://surly-cat.tumblr.com) if you feel so inclined. Also, I tag my progress on all my fics under [surlycat writes](http://surly-cat.tumblr.com/tagged/surlycat+writes). Hope you've enjoyed :D


End file.
